Methyl chloroformate → 1-methoxycarbonyl-S-methylisothiourea

HRID 597619Notes

Reaction equation

HRID 597619 reaction equation
S(O)(O)(=O)=O.[CH3:6][S:7][C:8](=[NH:10])[NH2:9].Cl[C:12]([O:14][CH3:15])=[O:13].[OH-].[K+]>O>[NH2:10][C:8](=[N:9][C:12](=[O:13])[O:14][CH3:15])[S:7][CH3:6]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 14797Potassium HydroxideHCID 752702-Methyl-2-thiopseudourea sulfate

Product 1

HCID 2935781-methoxycarbonyl-S-methylisothiourea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 69.5 parts 2-methyl-2-thiopseudourea sulfate and 47 parts of methyl chloroformate in 1000 parts water at 0° C is added dropwise 56.9 parts of potassium hydroxide in 200 parts of water. The reaction mixture is stirred at room temperature for 3 hours and then extracted with methylene chloride. The methylene chloride extract is dried and the solvent evaporated on a rotary evaporator to give 45 parts of methyl N-(1-amino-1-methylthiomethylene)carbamate melting at 72°-77° C.

Workup

  1. extractionextracted with methylene chloride
  2. extractionThe methylene chloride extract
  3. customis dried
  4. customthe solvent evaporated on a rotary evaporator

Sources & evidence

ORD record
ord-cb7a47f8d8914a7b9c79ea2e5a8badc6
Source dataset
uspto-grants-1977_03
Patent number
US04014924

Reaction notes

Loading…