4 -Phenyl Formamid

A mixture of jV-[(2-benzyl-3-methyl)phenyl]formamide (24. R1 = R3 = R4 = H R2 = Me 15 g, 68 mmol) in PPA (120 g) and POC1, (32 g. 208 mmol) was stirred at 120"C for 1.5 h. The mixture was cooled, diluted with cold H20. and basified by addition of aq KOH. The alkaline mixture was extracted with Et20, the extracts were dried (MgS04), and evaporated to give the crude product as an oily residue, which was purified by distillation under reduced pressure (bp 110 Q0.025 Torr). The distillate solidified on cooling to give the product as yellow needles yield 6g (43%) mp 68 C. 

CN (J , P )-( )-A-[2-hydroxy-5-[l-hydroxy-2-[[2-(4-methoxyphenyl)-l-methylethyl]amino]ethyl]phenyl]formamide... 

Man erhalt auf diese Weise z.B. aus N-Methyl-N-phenyl-formamid N-Methyl-anilin (70%), aus N.N-Diethyl-formamid Diethylamin (40%) und aus l,3-Bis-[formyl-phenyl-aminoj-propan 1,2-Dianilino-propan (79%). 

The reaction of tertiary formamides with sulfur tetrafluoride in the presence of potassium fluoride leads to replacement of both the carbonyl oxygen and formyl hydrogen atoms by fluorine. The formyl group is directly converted into the trifluoromethyl group to give N-(trifluoromethyl)amines which are isolated in almost quantitative yield (see Section 8.2.10.). Thus, dimethylformamide, diethylformamide, piperidinc-l-carbaldehyde, morpholine-1-carbaldehyde and ethyl(phenyl)formamide were converted into the corresponding A -(tri-fluoromethyl)amines 11.175... 

N-Formylation of 2-aminobenzothiazoles is achieved by treatment with 7V-phenyl formamide and two equivalents of benzenesulfonyl chloride in pyridine as a solvent <88CCC3ii>. Condensation of 2-aminobenzothiazole with dimethylacetylendicarboxylate in ethanol affords pyrimido-benzo-thiazolones (172). Similar heterocyclic systems are obtained when 2-aminobenzothiazoles are treated with ethylbenzoyl acetate in polyphosphoric add (Scheme 42) <88jhC949>. 

Phenylethyl) trichlorosilane. See 2-Phenethyltrichlorosilane Phenyl fluoride. See Fluorobenzene Phenylfluoroform. See Benzotrifluoride Phenyl formamide. See N-Phenylformamide N-Phenylformamide... 

Synonyms Carbanilaldehyde Formamidobenzene Formanilide Formylaniline N-Formylaniline Phenyl formamide... 

N -formylkynurenine 2-amino-4-[2-(formylamino)phenyl]-4-oxobutanoic acid. ) N-[2-(3-amino-l-oxopropyl)phenyl]formamide. 

O-Benzyloxy Phenyl Isocyanide 0-(Benzyloxy)phenyl formamide (li)... 

Eig. 7. CycHc voltammograms for the reduction of 1.0 mAf [2,2 -ethylene-bis(nitrilomethyHdyne)diphenolato]nickel(II) in dimethyl formamide at a glassy carbon electrode, in A, the absence, and B and C the presence of 2.0 and 5.0 mAf 6-iodo-l-phenyl-l-hexyne, respectively (14). 

A combination of the preceding type of synthesis and of cyclization of 4-amino-5-arylazopyrimidine can be seen in the novel procedure of Richter and Taylor. Proceeding from phenylazomalonamide-amidine hydrochloride (180), they actually close both rings in this synthesis. The pyrimidine ring (183) is closed by formamide, the triazole (181) one by oxidative cyclization in the presence of cupric sulfate. Both possible sequences of cyclization were used. The synthetic possibilities of this procedure follow from the combination of the two parts. The synthesis was used for 7-substituted 2-phenyl-l,2,3-triazolo[4,5-d]-pyrimidines (184, 185). An analogous procedure was employed to prepare the 7-amino derivatives (188) from phenylazomalondiamidine (186). 

A mixture of 4-carbamoyl-4-N-anilinopiperidine and formamide is heated for 12 hours at 170°C. After cooling, the reaction mixture is divided between 100 parts water and 900 parts chloroform. The organic layer is separated, dried over MgSO, filtered and the filtrate is evaporated. The semisolid residue is stirred in ethyl acetate. The undissolved part is filtered off, washed with ethyl acetate, and dried, yielding 1-oxo-4-phenyl-2,4,8-triazaspiro-(4.5)decane. 

So erhalt man z. B. aus 1-Jod-decan in DMF/TEAPan Quecksilber lediglich bei-1,1 V [vs. Cd(FIg)/CdCl2/NaCl] ausschlieBlich Didecyl-quecksilber ansonsten werden wech-selnde Gemische von Decan, Decen-(1), Decanol-(l) sowic /V-Methyl-N-decyl-formamid (bei — 1,9 V 40%d-Th.) erhalten7. Zur Reduktion von 3-Brom-1-phenyl-propan zu Propyl- benzol s. S. 619. 

Benzenediamine (199) and C-(2-chloro-2-phenylacetyl)formamide (200) gave 3-phenyl-3,4-dihydro-2-quinoxalinecarboxamide (201), formulated as its 1,4-dihydro tautomer (EtOH, reflux, 6 h 56%) in contrast, the same substrate (199) with methyl C-(2-chloro-2-phenylacetyl)formate cyanohydrin (202) gave methyl 3-phenyl-2-quinoxalinecarboxylate (203), presumably by aerial oxidation of a dihydro precursor (MeCN, reflux, 12 h 7%). ... 

The reaction with disubstituted formamides and phosphorus oxychloride, called the Vilsmeier or the Vilsmeier-Haack reaction,is the most common method for the formylation of aromatic rings. However, it is applicable only to active substrates, such as amines and phenols. An intramolecular version is also known.Aromatic hydrocarbons and heterocycles can also be formylated, but only if they are much more active than benzene (e.g., azulenes, ferrocenes). Though A-phenyl-A-methyl-formamide is a common reagent, other arylalkyl amides and dialkyl amides are also used. Phosgene (COCI2) has been used in place of POCI3. The reaction has also been carried out with other amides to give ketones (actually an example of 11-14),... 

In triphenyl compounds, quite symmetric structures result with larger donors. In the DMF adduct of triphenyltinsaccharin165, the three phenyls lie almost symmetrically in the equatorial plane (CSnC from 116°-124° Sn-C 212.5 pm) and the axial O from the formamide and N from the benzisothiazolone are near-linear axial (NSnO = 176° Sn-N = 224.2 pm, Sn-O = 240.2 pm). 

Materials. Reagent grade solvents, dimethyl formamide (DMF), dimethyl acetamide (DMAC), dimethyl sulfoxide (DMSO) and methanol were purchased from Baker, stored over molecular sieves once opened, and used without further purification. Aminoethane thiosulfuric acid (AETSA) purchased from Kodak, and Taurine, purchased from Alfa were purified by recrystallization. Each was thrice recrystallized from hot, deionized water. The crystalline precipitate was dried (48 hours at 40 °C) in-vacuo and subsequently stored in a desiccator. Benzophenone (BP) was purchased from Aldrich Chemical Company. QUANTACURE BTC (BTC), (4-benzolybenzyl) trimethylammonium chloride, was used as supplied by Aceto, Inc., Flushing, New York. Phenyl glycidyl ether (PGE) was purchased from MCB, distilled in-vacuo. and stored at -15 °C. Epon 828 was used as supplied bv Shell Chemical Company. The epoxy equivalent weight (EEW) for Epon 828 determined by an appropriate titration, was found to be 187.7. 

Miyata N, Seki T, Tanaka Y, Omura T, Taniguchi K, et al. 2005. Beneficial effects of a new 20-hydroxyeicosatetrae-noic acid synthesis inhibitor, TS-011 [N-(3-chloro-4-morpholin-4-yl) phenyl-N -hydroxyimido formamide], on hemorrhagic and ischemic stroke. J Pharmacol Exp Ther 314 77-85. 

FIGURE 8 Analysis of the test mixture with (A) the SDS MEKC system containing 10 mM phosphate buffer (pH 7.5), 60 mM SDS, and 10% acetonitrile and (B) the CTAB MEKC system containing 25 mM phosphate buffer (pH 7.5), 10 mM CTAB, and 10% acetonitrile. Peaks I formamide 2 pyridine 3 aniline 4 meta-cresol 5 phenyl acetate 6 nitrobenzene 7 benzoic acid 8 thiamine 9 ethyl benzoate. (Reprinted from reference 270, with permission.)... 

In the hands of other workers 485), however, the method has given less favourable results, affording much lower yields, even on prolonged refluxing in formamide. The product from phenylbiguanide and formamide was formulated as 3-phenyl- 536) and not 6-phenylguanamine (compare ref. 476). 

Unsubstituted species 114a is prepared from tropone 112 by cyclization with formamide (61BCI312) or with ethoxymethylene acetates and pyrolysis of intermediate oxazolines 115e-g (60NKZ509 61BCJ611). 2-Phenyl derivative 114d is obtained from 2-methoxy-7-(benzoylamino)tropone with... 

Araki et al. have found that La wesson s reagent, 2,4-bis(4-methoxyphenyl)-l,3-dithiaphos-phetane-2,4-disulflde, provides a convenient one-step conversion of mesoionic olates to mesoionic thiolates <88BCJ2977>. Thus 3-phenyl-1,2,3,4-thiatriazolium-5-olate (170) was converted to (171) in high yield by refluxing for 50 min in benzene (Equation (14)). This eompound had previously been prepared from compound (161 R = Ph) by treatment with sodium sulfide in aqueous dimethyl-formamide at room temperature <79JCS(Pi)732>. 

Auch Ammoniumformiat wird gelegentlich als Ammoniak-Quelle verwendet. Dadurch gelingt bei der Umsetzung von 2-Chlor-3-oxo-3-phenyl-propansaure-ethylester mit Formamid zu 5(4)-Ethoxycarbonyl-4(5)-phenyl-imidazol (37%) in einer drucklosen Reaktion ebenfalls eine Sen-kung der Reaktionstemperatur auf 135°50,... 

---