Methyl chloroformate → HCID 178502039, compound

HRID 1758883Notes

Reaction equation

HRID 1758883 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+].[CH:18]1([CH2:21][S:22][C:23]2[CH:28]=[CH:27][C:26]([NH2:29])=[C:25](N)[CH:24]=2)[CH2:20][CH2:19]1>O.CO.C(O)(=O)C>[CH:18]1([CH2:21][S:22][C:23]2[CH:28]=[CH:27][C:26]3[NH:29][C:8]([NH:9][C:12](=[O:13])[O:14][CH3:15])=[N:10][C:25]=3[CH:24]=2)[CH2:19][CH2:20]1

Participants

8

Reactant 4

HCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 752702-Methyl-2-thiopseudourea sulfateHCID 20284437HCID 20284437, compound

Product 1

HCID 178502039HCID 178502039, 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 water 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. The total amount of 4-(cyclopropylmethyl)thio-o-phenylenediamine from above in 50 ml of methanol is then added and the mixture is refluxed for 2 hours. The alcohol is removed in vacuo and water is added. The resulting solid is filtrated off and crystallized from glyme-acetonitrile to yield, 3.9 g, m.p. 228°-231°.

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 water
  5. additionis added
  6. filtrationThe resulting solid is filtrated off
  7. customcrystallized from glyme-acetonitrile
  8. customto yield

Sources & evidence

ORD record
ord-3b304a051e6b41249ee60856cd1b159d
Source dataset
uspto-grants-1982_07
Patent number
USRE030990

Reaction notes

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