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Ra | Yield,b (%) | Obs. mp,c (°C) | Lit. mp, (°C) | |
3,4-(MeO)2C6H3- | 89 | 80-81 | 81d | |
p-MeC6H4- | 84 | 98-99 | 99-101e | |
C6H5- | 95 | 45-46 | 47-48.5e | |
p-ClC6H4- | 94 | 113-115 | 115-117e | |
p-NO2C6H4- | 70f | 177-178 | 177.5-178g | |
C6H5CH2- | 95 | 64-65 | 65h | |
CH3(CH2)8- | 90 | < r.t. | – | |
CH3(CH2)14- | 73 | 61-62 | 61-62i | |
aPrepared from the corresponding carboxylic acid or acid chloride. |
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bRefers to pure isolated and characterized product. |
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cDetermined in capillary tubes and uncorrected. |
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dBrunner, O.; Wöhrl, R. Monatsh. 1933, 63, 374-384. |
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eFujisaki, S.; Tomiyasu, K.; Nishida, A.; Kajigaeshi, S. Bull. Chem. Soc. Jpn. 1988, 61, 1401-1403. |
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fOvernight reflux. |
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gHegarty, A. F.; Frost, L. N. J. Chem. Soc., Perkin Trans. 2 1973, 1719-1728. |
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hChabrier de la Saulnière, P. Ann. Chim. 1942, 17, 353-370. |
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iReference 3. |
Appendix
Chemical Abstracts Nomenclature (Collective Index Number);
(Registry Number)
Methyl N-(p-methoxyphenyl)carbamate: Carbamic acid, (4-methoxyphenyl)-, methyl ester (9); (14803-72-6)
p-Methoxybenzamide: Benzamide, 4-methoxy- (9); (3424-93-9)
N-Bromosuccinimide: Succinimide, N-bromo- (8); 2,5-Pyrrolidinedione, 1-bromo- (9); (128-08-5)
1,8-Diazabicyclo[5.4.0]undec-7-ene: DBU: Pyrimido[1,2-a]azepine, 2,3,4,6,7,8,9,10-octahydro- (8,9); (6674-22-2)