Phenyl isocyanate → 2-(4-Chloro-2-fluorophenyl)-3-(N-phenylcarbamoylthio)-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

HRID 647413Notes

Reaction equation

HRID 647413 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.[C:20]1([N:26]=[C:27]=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>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:27](=[O:28])[NH:26][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[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 7672Phenyl isocyanateHCID 132575922-(4-chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-3-mercapto-1H-isoindol-1-one

Product 1

HCID 132524162-(4-Chloro-2-fluorophenyl)-3-(N-phenylcarbamoylthio)-2,3,4,5,6,7-hexahydro-1H-isoindol-1-oneYield 72%

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 1.3 g of phenyl isocyanate, together with one drop of triethylamine, was added to the solution, followed by stirring at room temperature for 3 hours. The dichloromethane was distilled off under reduced pressure, and the residue was purified by means of column chromatography with the use of silica gel (developing solvent of acetonehexane), thereby producing 3.0 g (yield of 72%) of the subject compound in white crystals, m.p. 135°-136° C.

Workup

  1. distillationThe dichloromethane was distilled off under reduced pressure
  2. customthe residue was purified by means of column chromatography with the use of silica gel (developing solvent of acetonehexane)

Sources & evidence

ORD record
ord-974cb67e1213421d96fdd2fb1b1d82fe
Source dataset
uspto-grants-1983_10
Patent number
US04409018

Reaction notes

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