Methyl chloroformate → HCID 178460721, compound

HRID 614559Notes

Reaction equation

HRID 614559 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+].[CH2:18]([S:21][C:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[C:24](N)[CH:23]=1)[CH:19]=[CH2:20]>O.CO.C(O)(=O)C>[CH2:18]([S:21][C:22]1[CH:27]=[CH:26][C:25]2[NH:28][C:8]([NH:9][C:12](=[O:13])[O:14][CH3:15])=[N:10][C:24]=2[CH:23]=1)[CH:19]=[CH2:20]

Participants

8

Reactant 4

HCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 752702-Methyl-2-thiopseudourea sulfateHCID 21328030HCID 21328030, compound

Product 1

HCID 178460721HCID 178460721, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 5.7 g of 2-methyl-2-thiopseudourea sulfate in 3.4 ml of water there is added at 0° 3.6 ml of methyl chloroformate. The mixture is stirred for 10 minutes at this temperature. Then, there is added dropwise 7.6 ml of 25% NaOH. The temperature is kept below 25° and the mixture is stirred for 10 minutes. Then, 3.8 ml of acetic acid is added and again the temperature is kept below 25°. After a stirring period of 10 minutes, there is added the total of 4-(2-propenylthio)-o-phenylenediamine from Example 1B dissolved in 10 ml of methanol and the mixture is refluxed for one hour. The resulting solid is filtered off, washed with water and dried to yield 4 g. Crystallization from acetonitrile furnishes the analytically pure title compound, m.p. 197°-198°.

Workup

  1. customis kept below 25°
  2. stirringthe mixture is stirred for 10 minutes
  3. customis kept below 25°
  4. waitAfter a stirring period of 10 minutes
  5. temperaturethe mixture is refluxed for one hour
  6. filtrationThe resulting solid is filtered off
  7. washwashed with water
  8. customdried
  9. customto yield 4 g
  10. customCrystallization from acetonitrile

Sources & evidence

ORD record
ord-b8b3100525d746f396e9168e4a46b5bb
Source dataset
uspto-grants-1979_03
Patent number
US04145431

Reaction notes

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