Ethyl isothiocyanate → HCID 13252427, compound

HRID 647414Notes

Reaction equation

HRID 647414 reaction equation
[Br: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.[CH2:20]([N:22]=[C:23]=[S:24])[CH3:21]>ClCCl.C(N(CC)CC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:16]([S:17][C:23](=[S:24])[NH:22][CH2:20][CH3:21])[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 10966Ethyl isothiocyanateHCID 13252420HCID 13252420, compound

Product 1

HCID 13252427HCID 13252427, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

In 20 ml of dichloromethane was dissolved 3.4 g of 2-(4-bromo-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-3-mercapto-1H-isoindol-1-one, and 1.0 g of ethyl 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 3.8 g (yield of 88%) of the subject compound. Recrystallization from ethanol yielded white crystals, m.p. 130°-131° 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-13e79397c84146319629c9c238e27b99
Source dataset
uspto-grants-1983_10
Patent number
US04409018

Reaction notes

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