Carbon Disulfide → 3-Fluorobenzyl isothiocyanate

HRID 34272

Reaction equation

HRID 34272 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][NH2:6].C1(N=C=NC2CCCCC2)CCCCC1.[C:25](=S)=[S:26]>CCOCC>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][N:6]=[C:25]=[S:26]

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 10868DicyclohexylcarbodiimideHCID 668533-Fluorobenzylamine

Product 1

HCID 27372753-Fluorobenzyl isothiocyanate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 3-fluorobenzylamine (6.26 g., 0.05 mole) in ether (10 ml.) was added dropwise to a solution of dicyclohexylcarbodiimide (10.3 g., 0.05 mole) and carbon disulfide (20 ml., 0.333 mole) in ether (60 ml.) at -5 °to -10° C. and the mixture was stirred for 17 hours at 25° C. The mixture was filtered, and the solvent was removed under vacuum. The resulting oil was dissolved in hexane-ethyl acetate (19:1), filtered and the solvent removed under vacuum. The oil was then dissolved in hexane-ethyl acetate (9:1) and purified by flash chromatography (silica) to give 3-fluorobenzylisothiocyanate as an oil (8.14 g., 97%).

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent was removed under vacuum
  3. dissolutionThe resulting oil was dissolved in hexane-ethyl acetate (19:1)
  4. filtrationfiltered
  5. customthe solvent removed under vacuum
  6. dissolutionThe oil was then dissolved in hexane-ethyl acetate (9:1)
  7. custompurified by flash chromatography (silica)

Sources & evidence

ORD record
ord-1dee99fb960a4de0998f5436fd2a4c6b
Source dataset
uspto-grants-1988_08
Patent number
US04761415

Linked notes

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