Methyl isothiocyanate → 2-(4-Chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-3-(N-methylthiocarbamoylthio)-1H-isoindol-1-one

HRID 647415Notes

Reaction equation

HRID 647415 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:16]([SH:17])[C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9]2=[O:18])=[C:4]([F:19])[CH:3]=1.[CH3:20][N:21]=[C:22]=[S:23]>ClCCl.C(N(CC)CC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:16]([S:17][C:22](=[S:23])[NH:21][CH3:20])[C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9]2=[O:18])=[C:4]([F:19])[CH:3]=1

Participants

5

Reactant 2

HCID 11167Methyl isothiocyanateHCID 132575922-(4-chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-3-mercapto-1H-isoindol-1-one

Product 1

HCID 132575972-(4-Chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-3-(N-methylthiocarbamoylthio)-1H-isoindol-1-oneYield 94%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

In 20 ml of dichloromethane was dissolved 3.0 g of 2-(4-chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-3-mercapto-1H-isoindol-1-one, and 0.8 g of methyl isothiocyanate, together with one drop of triethylamine, was added to the solution, followed by stirring at room temperature for 5 hours. The dichloromethane was distilled off under reduced pressure, and the resulting crystals were washed with cold ethanol and dried, thereby producing 3.5 g (yield of 94%) of the subject compound. Recrystallization from ethanol yielded white crystals, 112°-114° C.

Workup

  1. distillationThe dichloromethane was distilled off under reduced pressure
  2. washthe resulting crystals were washed with cold ethanol
  3. customdried

Sources & evidence

ORD record
ord-e8ecead534d44237b2f8763b4dce8505
Source dataset
uspto-grants-1983_10
Patent number
US04409018

Reaction notes

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