5-Anilino-3-methyl

Anilino-3-methyl-l,2,4-thiadiazole (but not the 3-phenyl analog) forms a mono-tosyl derivative,129 which is degraded to toluene-p-Bulfonanilide (217) on reductive hydrolysis this again establishes a 5-sulfonamido structure (215) for the derivative.129... 

Anilino-3-methyl-l-phcnyl- 634 5(3)-Anilino-3(5)-methyl-4-phenylazo- 629 3(5)-Anilino-5(3)-phenyl- 458 4-(4-Anilinosulfonyl-phenylazo)-3-methyl-l-(4-... 

Boran Brom-(4-ethyl-anilino)-methyl- XIII/3b, 142... 

Triazin 5-[Chlor-(N-methyl-anilino)-methyl]-3-methylthio-E9c, 631 (H - CHQ—NR2)... 

Amino-2-methyl-l-phenyl- 1244 l-(Anilino-methyl)- 261 Benzylamino- 2034... 

In an overwhelming majority of cases the diamine 1 is (S)-2-(anilino-methyl)pyrrolidine (Ar = Ph), easily obtained from L-glutamic acid and nowadays commercially available. 

Anilino vinyl derivatives of thiazolium (30, R = H) or acetanilido (30, R = C0CH3), as well as formyl methylene 30b (methods E-G), give asymmetrical dyes when condensed with a methyl reactive group of another species (Scheme 42). Mesosubstituted symmetrical or unsymmet-rical thiazolocyanines are obtainable via /S-alkylmercaptovinyl thiazolium derivatives (32) (methods H and I) (Scheme 43). a or /S carbon atoms of the trimethine chain can be substituted by acetyl when a dye is treated with acetic anhydride (method L). The hydrolysis of neocyanines lead to trimethine cyanine by fractional elimination of a composant chain (method K). 

In a similar way the use of the 2-methyl-3-isothiocyanato-4-thiocyanato-hept-3-ene (252) prepared from thiocyanogen and the oxoal-kylene phosphorane (251) yields the 2-anilino-4-propyl-5-isopropyl-thiazole (253) by condensation with aniline (Scheme 128). 

Naphth[2,l-d]oxazole, 2-methyl-oxidation, 6, 188 reactions, 6, 216 Naphthoxazoles, anilino-alkylation, 6, 189... 

Quinoline, amino-2-hydroxy-4-methyl-azo pigments from, 1, 334 Quinoline, 8-amino-6-methoxy-as antimalarial, 2, 517 Quinoline, 4-amino-2-methyl-protonation, 2, 341 Quinoline, anilino-3-substituted... 

Thiophene, 2-amino-3-cyano-5-phenyl-synthesis, 4, 888-889 Thiophene, 3-amino-4,5-dihydro-cycloaddition reactions, 4, 848 Thiophene, 2-amino-3-ethoxycarbonyl-ring opening, 4, 73 Thiophene, 2-amino-5-methyl-synthesis, 4, 73 Thiophene, 2-anilino-synthesis, 4, 923-924 Thiophene, aryl-synthesis, 4, 836, 914-916 Thiophene, 2-(arylamino)-3-nitro-synthesis, 4, 892 Thiophene, azido-nitrenes, 4, 818-820 reactions, 4, 818-820 thermal fragmentation, 4, 819-820 Thiophene, 3-azido-4-formyl-reactions... 

Deactivation in the anion formed under the reaction conditions prevents alkoxy-dechlorination of 4-chloro-2-quinolone (222) with boding alkoxide solution while 4-chloroquinoline and its 2-ethoxy and 2-anilino derivatives react. 4-Chloro-iV -methyl-2-quinolone reacts readily. 

Dichloro-l,3,5-triazanaphthalene and its 6-methyl derivative react at the 4-position (70-90% yields) with ammonia in dioxane (20°, 15 min) or in water (95°, 1.5 hr) and with diethylamine in dioxane (20°, 15 min). The dichloroazine yields the 4-(A-ethyl-anilino)-2-chloro derivative under acidic conditions. Amination of the 2,4-dithioxo derivative with concentrated ammonia (95°,... 

Similarly, for 2-(p-substituted-anilino)benzothiazoles (180 181), the relative proportions of the isomeric A -methyl derivatives produced on reaction with methyl iodide in neutral solution has been related to... 

A mixture of 65 parts 1 -[4,4-di-(4-fluoro-phenvl)butyl] -piperazine, 4.33 parts N-(2-chloro-acetyl)-2,6-dimethyl-aniline, 3.2 parts sodium carbonate, a few crystals of potassium iodide in 200 parts 4-methyl-2-pentanone is stirred and refluxed for 70 hours. After cooling there are added 70 parts water. The organic layer is separated, dried over potassium carbonate, filtered and evaporated. The oily residue is dissolved in 80 parts diisopropyl-ether and the solution is filtered hot. After cooling the filtrate at 0°C, the formed solid is filtered off and recystallized from 80 parts ether, yielding 1-[4,4-di-(4-fluoro-phenyl)butyl] -4-[(2,6-dimethyl-anilino-carbonvl)-mathyl] -piperazine MP 159°Cto 161°C. 

The synthesis of 987 from 985 via 986 has been reported (83S759) by reaction of 985 with aryl isothiocyanates under neutral conditions. The reaction of 4-amino-6-anilino[l,2,4]triazine 988 with methyl iodide and then carbon disulfide gave 989 (90MI3, 90MI9). 

N,N-Dimethyl-aniHn 6,2 g (29 mMol) Nickel-(N-Methyl-anilino)-dithiocarbonat werden portionsweise zu 2,1 g (55 mMol) Lithiumalanat in 300 mi abs. Diathylather gegeben and 4 Stdn. unter RiickfluB erhitzt. Man ver-setzt die Mischung mit feuchtem Diathylather, Wasser und verd. Salzsaure und macht nach Zugabe von 10 g Weinsaure die waBr. Phase alkalisch. Die ausgeschicdcnc Base wird mit Diathylather extrahiert Ausbeute 3,34 g (95"/ d.Th.) Kp 193°. 

Methyl-anilino)-l -oxo-1,2-dipyridyl-(2)- 610 2-(4-Methyl-phenyIimino)- 1-oxo-1,2-dipyridyl-(2)-... 

Amino-l-(4-methyl-phenyl)- 354 2-Amino-l-phenyl- 117f., 354 2-Anilino-2-phenyl- 136 f. 

Dimethoxy-pentadien-(l,3) und Natrium-cyano-trihydrido-borat 434 5-(N-Methyl-anilino)- 303... 

Anilino-5 -nitroaniline (170) gave 2,3-dimethyl-6-nitro-l-phenylquinoxaIi-nium perchlorate (171) (Ac2, HCIO4, Bu0H-Et20-H20, 20°C, 20 min 84%) and thence 2-methyl-3-methylene-7-nitro-4-phenyl-3,4-dihydroqui-... 

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