Thiosemicarbazide → HCID 53934318, compound

HRID 2082052Notes

Reaction equation

HRID 2082052 reaction equation
Cl.[C:2](=[NH:10])([O:7][CH2:8][CH3:9])[CH2:3][CH2:4][CH2:5][CH3:6].N[NH:12][C:13]([NH2:15])=[S:14].C(Cl)Cl.CO>CN(C=O)C>[C:2](=[N:10][NH:12][C:13]([NH2:15])=[S:14])([O:7][CH2:8][CH3:9])[CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 2723789Thiosemicarbazide2×HCID 12283341Ethyl pentanimidate hydrochlorideHCID 21226129Dichloromethane methanol2×

Product 1

HCID 53934318HCID 53934318, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-420ecd46eff6438e970b20d64714a050
Source dataset
uspto-grants-1993_02
Patent number
US05187179

Reaction notes

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