2-Methyl-2-thiopseudourea → Benzyl [amino(methylsulfanyl)methylene]carbamate

HRID 67706

Reaction equation

HRID 67706 reaction equation
[CH3:1][S:2][C:3](=[NH:5])[NH2:4].[CH2:6]([O:13][C:14](Cl)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[Na+]>O>[CH2:6]([O:13][C:14]([NH:5][C:3](=[NH:4])[S:2][CH3:1])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 51422-Methyl-2-thiopseudoureaHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide

Product 1

HCID 140362141Benzyl [amino(methylsulfanyl)methylene]carbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

13.9 g (0.1 mole) of S-methyl-isothiourea are dissolved in 50 ml of water, cooled to a temperature of 0° to 5° C., and at this temperature and with constant stirring 15 ml (0.1 mole) of chloroformic acid benzyl ester and 50 ml of 4 N sodium hydroxide are added in about 20 minutes. The precipitate formed is filtered, washed three times with 50 ml of cold water, then three times with 50 ml of n-hexane, and finally dried over phosphorpentoxide in vacuo. Yield 15.7 g (70 percent) of the named compound. M.p.: 74° to 75° C.; RF1 0.70 to 0.75.

Workup

  1. temperaturecooled to a temperature of 0° to 5° C.
  2. additionare added in about 20 minutes
  3. customThe precipitate formed
  4. filtrationis filtered
  5. washwashed three times with 50 ml of cold water
  6. dry with materialthree times with 50 ml of n-hexane, and finally dried over phosphorpentoxide in vacuo

Sources & evidence

ORD record
ord-a20db19e16264b86af370111a4c273e0
Source dataset
uspto-grants-1982_08
Patent number
US04346078

Linked notes

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