反应详情

A solution of 10.79 g (65 mmol) of ethyl valerimidate hydrochloride [prepared by method of A. J. Hill and I. Rabinowitz, J. Am. Chem. Soc., 48, 734 (1926)] in 130 ml of dry DMF was stirred at room temperature as 5.91 g (65 mmol) of thiosemicarbazide was added. Stirring was continuted under N2. After 2.5 hours, by which time TLC (19:1 CH2Cl2 -MeOH) indicated complete conversion of thiosemicarbazide to a higher Rf product, the mixture was partitioned between 1 L of H2O, then dried over MgSO4, filtered, and concentrated in vacuo. The residual oil, upon drying in vacuo (<1 mm) overnight, solidified to yield 11.05 g (84%) of nearly white solid, mp 73°-74.5° C.; homogeneous by TLC in 97:3 CH2Cl2 -MeOH. NMR indicated a mixture of syn and anti isomers.

1. additionwas added
2. customthe mixture was partitioned between 1 L of H2O
3. dry with materialdried over MgSO4
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe residual oil, upon drying in vacuo (<1 mm) overnight
7. customto yield 11.05 g (84%) of nearly white solid, mp 73°-74.5° C.
8. additiona mixture of syn and anti isomers