Carbon Disulfide → 3-Fluoro-4-(2,2,2-trifluoroethoxy)benzyl isothiocyanate
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][C:12]([F:15])([F:14])[F:13])[CH2:5][NH2:6].C1CCC(N=C=NC2CCCCC2)CC1.[C:31](=S)=[S:32]>C(OCC)C>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][C:12]([F:13])([F:14])[F:15])[CH2:5][N:6]=[C:31]=[S:32]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
The crude 3-fluoro-4-(2,2,2-trifluoroethoxy)benzylamine (7.54 g) was added dropwise to a mixture of 7.45 g of DCC, 15 ml of carbon disulfide and 30 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 3 hours. The reaction mixture was filtered, and the residue was washed with ethyl 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
Workup
- customwas returned to room temperature
- waitit was left
- filtrationThe reaction mixture was filtered
- washthe residue was washed with ethyl ether
- customThe solvent was evaporated under reduced pressure
- customThe resulting oily product was purified by column chromatography (silica gel
Sources & evidence
- ORD record
- ord-47dcedfaae6a43fb805a229d95f388a5
- Source dataset
- uspto-grants-1991_06
- Patent number
- US05021412
Reaction notes
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