Methyl chloroformate → HCID 178502042, compound

HRID 616920Notes

Reaction equation

HRID 616920 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([CH2:24][S:25][C:26]2[CH:31]=[CH:30][C:29]([NH2:32])=[C:28](N)[CH:27]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>O.CO>[CH:18]1([CH2:24][S:25][C:26]2[CH:31]=[CH:30][C:29]3[NH:32][C:8]([NH:9][C:12](=[O:13])[O:14][CH3:15])=[N:10][C:28]=3[CH:27]=2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

7

Reactant 4

HCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 752702-Methyl-2-thiopseudourea sulfateHCID 20532843HCID 20532843, compound

Product 1

HCID 178502042HCID 178502042, compound

Reagents, catalysts & solvents 2

HCID 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 the total amount of 4-(cyclohexylmethyl)thio-o-phenylenediamine from the above reaction in 50 ml of methanol is added and the mixture is refluxed for 2 hours. The alcohol is removed in vacuo and water is added. The resulting solid is filtered off and crystallized from CH3CN to yield 2.5 g, m.p. 200°-204° C.

Workup

  1. stirringthe mixture is stirred for 15 minutes
  2. additionis added
  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 filtered off
  7. customcrystallized from CH3CN
  8. customto yield 2.5 g, m.p. 200°-204° C.

Sources & evidence

ORD record
ord-a044dba33caa4010bd9ca993bc068cc6
Source dataset
uspto-grants-1978_02
Patent number
US04076828

Reaction notes

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