Methyl chloroformate → HCID 178502040, compound

HRID 838995Notes

Reaction equation

HRID 838995 reaction equation
S(O)(O)(=O)=O.CS[C:8](=[NH:10])[NH2:9].Cl[C:12]([O:14][CH3:15])=[O:13].[OH-].[Na+].[Cl:18][C:19]1([Cl:32])[CH2:21][CH:20]1[CH2:22][S:23][C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[C:26](N)[CH:25]=1>O.CO.C(O)(=O)C>[Cl:32][C:19]1([Cl:18])[CH2:21][CH:20]1[CH2:22][S:23][C:24]1[CH:29]=[CH:28][C:27]2[NH:30][C:8]([NH:9][C:12](=[O:13])[O:14][CH3:15])=[N:10][C:26]=2[CH:25]=1

Participants

8

Reactant 4

HCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 752702-Methyl-2-thiopseudourea sulfateHCID 20532837HCID 20532837, compound

Product 1

HCID 178502040HCID 178502040, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 9 g of 2-methyl-2-thiopseudourea sulfate in 6 ml of H2O there is added 5.7 ml of methyl chloroformate at 0° C and the mixture is stirred for 15 minutes. Then there is added 12 ml of 25% NaOH dropwise and the mixture is stirred for 15 minutes. Then there is added 6 ml of acetic acid dropwise and the mixture is stirred for 15 minutes. Then the total amount of 4-[(2,2-dichlorocyclopropyl)methyl]thio-o-phenylenediamine from above in 50 ml of methanol is added and the mixture is refluxed for 2 hours. The alcohol is removed in vacuo and H2O is added. The resulting solid is filtered off and crystallized from glyme to yield 5.4 g, m.p. 211-213°.

Workup

  1. stirringthe mixture is stirred for 15 minutes
  2. stirringthe mixture is stirred for 15 minutes
  3. temperaturethe mixture is refluxed for 2 hours
  4. customThe alcohol is removed in vacuo and H2O
  5. additionis added
  6. filtrationThe resulting solid is filtered off
  7. customcrystallized from glyme
  8. customto yield 5.4 g, m.p. 211-213°

Sources & evidence

ORD record
ord-31e8a5fa773f451c874040e52d18167b
Source dataset
uspto-grants-1978_06
Patent number
US04093732

Reaction notes

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