Cinnamoyl chloride

As with poly(vinyl alcohol), poly(vinyl cinnamate) is prepared by chemical modification of another polymer rather than from monomer . One process is to treat poly(vinyl alcohol) with cinnamoyl chloride and pyridine but this is rather slow. Use of the Schotten Baumann reaction will, however, allow esterification to proceed at a reasonable rate. In one example poly(vinyl alcohol) of degree of polymerisation 1400 and degree of saponification of 95% was dissolved in water. To this was added a concentrated potassium hydroxide solution and then cinnamoyl chloride in methyl ethyl ketone. The product was, in effect a vinyl alcohol-vinyl cinnamate copolymer Figure 14.8)... 

The isomeric -cinnamylcocaine (methylcinnamoyl-d- -ecgonine) prepared by Einhorn and Deckers by the action of cinnamoyl chloride at 150-60° on d-i/r-ecgonine methyl ester, crystallises in prisms, m.p. 68°, [ Id + 2° (EtOH). The hydrochloride, B. HCl, forms needles, m.p. 186° the platinichloride, needles, m.p. 208°, and the aurichloride orange needles, m.p. 164°. 

Acylation of the monosubstituted piperazine, 99 (obtainable by the protection-deprotection scheme outlined above), with cinnamoyl chloride gives the corresponding amide (100). Reduction of the carbonyl by means of lithium aluminum hydride affords cinnarizine (101). ... 

A solution of 1-piperazino ethyl acetate (Q2 mol) in benzene (300 ml) is treated with 3,4.5-trimethoxy cinnamoyl chloride (0,2 mol) in the presence of sodium bicarbonate (0.3 mol). After contacting for one hour at room temperature, the mixture is refluxed for a further hour. The benzene solution is then treated with an aqueous solution of sodium bicarbonate. After evaporation of the solvent, a solid product is obtained which is recrystallized from isopropyl ether. Melting point = 96°C. This base, when treated with hydrochloric acid, gives a hydrochloride having a melting point of 200°C with decomposition. By the action of malaic acid the acid maleate is obtained, having a melting point of 130°C. 

Cinnamoyl chloride Benzhydryl piperazine Lithium aluminum hydride... 

This compound can be prepared by the reaction of cinnamoyl chloride with benzhydryl-piperazine. The reaction is carried out in dry benzene under reflux. The benzene is then evaporated, the residue taken up in chloroform, washed with dilute HCI and then made alkaline. 

Cortisone acetate Demegestone Fluocortolone Medrogestone Norethindrone Chromic anhydride Fludiazepam HCI Nimetazepam Sulpro stone Cinchonidine Melphalan Cinnamoyl chloride Cinnarizine... 

C,H802 140-10-3) see Tolterodine cinnamoyl chloride (C9H7CIO 102-92-1) see Cinmetacin cinnamyl alcohol... 

Scheme 5 Cathodic reduction of cinnamoyl chloride to the corresponding ketene dimer [70b].

Reaction of poly(vinyl alcohol) with cinnamoyl chloride yields polymers that produce photocrosslinked resists for microelectronic applications. 

Chloroacetyl chloride and 2-bromoacetyl bromide N-acylated without a catalyst but 2-chloroacetic anhydride required concentrated sulfuric acid. ° 3-Chloro- and 3-bromopropionyl chlorides 9-acyl-ated without a catalyst as did cinnamoyl chloride " and phosgene, the last producing 9-chloroformyIcarbazole. ... 

N-Acylation of 2-methyl-5,6-dihydro-4/f-l,3-thiazine with cinnamoyl chloride in the presence of triethylamine furnishes ( )-l-(2-methylenetetrahydro-l,3-thiazin-3-yl)-3-arylprop-2-en-l-ones 122. These products undergo hydrolysis readily due to the j jA -ketene acetal-type bonds present in the molecules and are therefore not stable. Thus ( )-3-(3-(4-methoxyphenyl)acrylamido)propyl ethanethioate 123 is isolated in 92% yield from the corresponding thiazine after column chromatography on Si02 or AI2O3 <2001S135>. 

Base-catalyzed cyclization of A -benzoyl-a-chloroacetamide is a classical method used to prepare 2-phenyl-4(5//)-oxazolone. Extension of this methodology to the A -aroylcinnamides 35 afforded a series of 5-arylidene analogues 37 albeit in unstated yield (Scheme 6.12). " Thus, acylation of the sodium salt of a benzamide with a cinnamoyl chloride gave the imides 35 that were converted to 36 via a bromination-dehydrobromination sequence. Cyclization to 37 was affected with sodium hydride in 1,2-dimethoxyethane (DME). The authors noted that catalytic reduction of 37 afforded the 5-(arylidene)oxazolidine from which 37 could be regenerated in the presence of air. 

From 2-aminopyridine and cinnamoyl chloride Tkachenko et al25 prepared the amide (148) and transformed it to 2-oxopyrido[l,2-a]pyrimidine (149) by heating in ethanol. 

The formation of naphtho[6c]thiophene-3-ones 106 takes place on acylation of 2-substituted benzo[b]thiophenes 103 with cinnamoyl chloride (78AP710, 78LA627 79LA965). Interestingly, the aromatization of the intermediate 105 occurs with elimination of benzene. Chalcone 104 also may be obtained on acetylation of benzo[fe]thiophene 103, followed by condensation of benzaldehyde with the methyl group of the 3-acetylbenzo[b]thiophene intermediate (79LA965). 

Sodium bicarbonate 3,4,5-Trimethoxy cinnamoyl chloride Maleic acid... 

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