Organic Chemistry International / 2010 / Article / Tab 1 / Research Article
Benzoylation of Amines sans Alkali: A Green Protocol in Neat Phase Table 1 Results of benzoylation of amines in neat phase (solvent-free condition) sans base# .
Entry Substrate Product Yielda (%) mp o C (lit. [31 ] mp o C) Time (min) 1 Aniline Benzanilide 92 164 (163) 3 2 2-Methylaniline 2-Methylbenzanilide 76 142 (143) 3 3 3-Methylaniline 3-Methylbenzanilide 91 125 (125) 3 4 4-Methylaniline 4-Methylbenzanilide 89 157 (158) 3 5 2-Chloroaniline 2-Chlorobenzanilide 95 99 (100) 3 6 3-Chloroaniline 3-Chlorobenzanilide 76 121 (120) 3 7 4-Chloroaniline 4-Chlorobenzanilide 95 191 (192) 3 8 3-Nitroaniline 3-Nitrobenzanilide 69 156 (155) 10 9 4-Methoxyaniline 4-Methoxybenzanilide 92 153–54 (154) 5 10 2-Aminobenzoic acid 2-(N -benzamido) benzoic acid 76 180 (182) 5 11 4-Aminobenzoic acid 4-(N -benzamido) benzoic acid 73 >250 (278) 5 12 Methyl anthranilate N -benzoyl methylanthranilate76 98-99 (100) 5 13 1-Naphthyl amine 1-N -benzamido-naphthalene 66 159 (161) 3 14 4-Amino pyridine N -(4-pyridyl) benzamide66 208–209 20 15 2-Amino thiazole N- (2-thiazolyl) benzamide70 150 (152 [30 ] ) 10 16 Benzyl amine N -benzyl benzamide88 105 (106) 3 17 Cyclohexyl amine N -cyclohexyl benzamide86 147–48 (148) 2 18 N,N -dimethyl hydrazineN,N -dimethyl benzamide75 166–67 10 19 Diphenyl amine N -benzoyl diphenyl amine67 180 (182) 25 20 Morpholine N -benzoyl morpholine58 73 (75) 20
# All the compounds give satisfactory spectral data (IR, NMR).
a Yield refers to the combined amounts of the first and second crop of crystallized product.