Carbon Disulfide → HCID 14774190, compound

HRID 1493212Notes

Reaction equation

HRID 1493212 reaction equation
[Cl:1][C:2](=[CH2:13])[CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1.C1CCC(N=C=NC2CCCCC2)CC1.[C:29](=S)=[S:30]>C(OCC)C>[Cl:1][C:2](=[CH2:13])[CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][N:10]=[C:29]=[S:30])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 10868DicyclohexylcarbodiimideHCID 14774189HCID 14774189, compound

Product 1

HCID 14774190HCID 14774190, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-10 °C

Procedure

6.7 g of 4-(2-chloro-2-propeneoxy)benzylamine was added dropwise to a mixture of 7.7 g of DCC, 20 ml of carbon disulfide and 100 ml of diethyl ether with stirring at -10° C. 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 and combined with the filtrate. The solvent was evaporated under reduced pressure. The resulting oily product was purified by column chromatography (silica gel; developing solvent hexane) to give 6.6 g of the desired 4-(2-chloro-2-propeneoxy)benzyl isothiocyanate as an oil.

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; developing solvent hexane)

Sources & evidence

ORD record
ord-863af259a5dc4523a0f739a7d7c0772c
Source dataset
uspto-grants-1991_06
Patent number
US05021412

Reaction notes

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