Carbon Disulfide → Benzyl Isothiocyanate

HRID 2166417Notes

Reaction equation

HRID 2166417 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16](=[S:18])=S.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CCOCC>[CH2:19]([N:26]=[C:16]=[S:18])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 7504BenzylamineHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 2346Benzyl IsothiocyanateYield 62%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Dicyclohexylcarbodiimide (10.3 g) and carbon disulphide (20 ml) are stirred in a round-bottomed flask with 20 ml of diethyl ether at -10° C. Benzylamine (5.35 g, 5.5 ml) in 20 ml ether is added slowly when a white precipitate forms immediately. The reaction mixture is stirred overnight, filtered and the ether removed in vacuo. The residue is suspended in ether, filtered and the ether removed in vacuo. The remaining oil is distilled under vacuum (0.5 mm, 100° C. approx.) to give benzylisothiocyanate as an oil (4.7 g, 62%).

Workup

  1. filtrationfiltered
  2. customthe ether removed in vacuo
  3. filtrationfiltered
  4. customthe ether removed in vacuo
  5. distillationThe remaining oil is distilled under vacuum (0.5 mm, 100° C. approx.)

Sources & evidence

ORD record
ord-a1f9af1cd7a94fe6a44d5afebd07246d
Source dataset
uspto-grants-1990_07
Patent number
US04945106

Reaction notes

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