Carbon Disulfide → 3,5-Difluorobenzyl isothiocyanate

HRID 34275

Reaction equation

HRID 34275 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH2:5][NH2:6].C1(N=C=NC2CCCCC2)CCCCC1.[C:26](=S)=[S:27]>CCOCC>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH2:5][N:6]=[C:26]=[S:27]

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 10868DicyclohexylcarbodiimideHCID 1452113,5-Difluorobenzylamine

Product 1

HCID 201291633,5-Difluorobenzyl isothiocyanate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 3,5-difluorobenzylamine (11.6 g., 0.081 mole) in ether (20 ml.) was added dropwise to a solution of dicyclohexylcarbodiimide (16.7 g., 0.081 mole) and carbon disulfide (32.4 ml., 0.539 mole) in ether (100 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-ether (19:1), filtered, and the solvent removed under vacuum. The oil was then dissolved in hexane and purified by flash chromatography (silica) to give 3,5-difluorobenzylisothiocyanate as an oil (5.40 g., 36%).

Workup

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

Sources & evidence

ORD record
ord-e1069c648cad4189ade825f4ea9c13e2
Source dataset
uspto-grants-1988_08
Patent number
US04761415

Linked notes

Loading…