Carbon Disulfide → 1-(Isothiocyanatomethyl)-4-(trifluoromethyl)benzene

HRID 1493206Notes

Reaction equation

HRID 1493206 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.C1CCC(N=C=NC2CCCCC2)CC1.[C:28](=S)=[S:29]>C(OCC)C>[F:1][C:2]([F:11])([F:12])[C:3]1[CH:10]=[CH:9][C:6]([CH2:7][N:8]=[C:28]=[S:29])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 10868DicyclohexylcarbodiimideHCID 768044-(Trifluoromethyl)benzylamine

Product 1

HCID 148010401-(Isothiocyanatomethyl)-4-(trifluoromethyl)benzene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

10 g of 4-trifluoromethylbenzylamine was added dropwise at -10° C. with stirring to a mixture of 11.78 g of DCC, 25 ml of carbon disulfide and 50 ml of diethyl ether. The temperature of the mixture was returned to room temperature, and it was left to stand for 12 hours. The reaction solution was filtered, and the residue was washed with diethyl ether. The filtrate and the washing were combined, and the solvent was evaporated under reduced pressure. The resulting oily product was purified by column chromatography silica gel; developing solvent hexane/ethyl acetate (10:1)]to give 11.15 g of the desired 4-trifluoromethylbenzyl isothiocyanate.

Workup

  1. customwas returned to room temperature
  2. waitit was left
  3. filtrationThe reaction solution was filtered
  4. washthe residue was washed with diethyl ether
  5. customthe solvent was evaporated under reduced pressure
  6. customThe resulting oily product was purified by column chromatography silica gel

Sources & evidence

ORD record
ord-b30a4bedf09f49578e3e6094a443e9a8
Source dataset
uspto-grants-1991_06
Patent number
US05021412

Reaction notes

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