Carbon Disulfide → 1-Tert-butyl-4-(isothiocyanatomethyl)benzene

HRID 1493204Notes

Reaction equation

HRID 1493204 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[C:28](=S)=[S:29]>C(OCC)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]=[C:28]=[S:29])=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 10868DicyclohexylcarbodiimideHCID 27356554-tert-Butylbenzylamine

Product 1

HCID 148010411-Tert-butyl-4-(isothiocyanatomethyl)benzene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

8.16 g of 4-t-butylbenzylamine was added dropwise at -10° C. with stirring to a mixture of 10.32 g of dicyclohexylcarbodiimide (DCC), 20 ml of carbon disulfide and 100 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 was combined with the washing, and the solvent was evaporated under reduced pressure. The resulting oily product was purified by column chromatography silica gel; developing solvent hexane/ethyl acetate (19:1) to give 8.41 g of the desired 4-t-butylbenzyl 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-ed537bc2ba8c4857a41a39433f70a3a9
Source dataset
uspto-grants-1991_06
Patent number
US05021412

Reaction notes

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