Methyl chloroformate → HCID 178502040, compound

HRID 1758886Notes

Reaction equation

HRID 1758886 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 cyystallized 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. customto yield 5.4 g, m.p. 211°-213°

Sources & evidence

ORD record
ord-60d8b7dd85d8491692b2a239cab8489c
Source dataset
uspto-grants-1982_07
Patent number
USRE030990

Reaction notes

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