Ethyl isothiocyanate → N-ethyl-2,2-bis(fluoromethyl)-6-trifluoromethyl-2H-1-benzopyran-4-carbothioamide
Reaction equation
Br[C:2]1[C:7]2[CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH2:18][F:19])([CH2:16][F:17])[CH:3]=1.C([Li])CCC.[CH2:25]([N:27]=[C:28]=[S:29])[CH3:26]>C(OCC)C>[CH2:25]([NH:27][C:28]([C:2]1[C:7]2[CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH2:18][F:19])([CH2:16][F:17])[CH:3]=1)=[S:29])[CH3:26]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
An amount (103 mg) of 4-bromo-2,2-bis(fluoromethyl)-6-trifluoromethyl-2H-1-benzopyran was dissolved in diethyl ether (0.3 ml); to the solution, 1.68 M n-butyllithium (0.18 ml) was added at 0° C. under a nitrogen atmosphere. After stirring the reaction mixture for 2 minutes, a diethyl ether solution (0.3 ml) of ethyl isothiocyanate (34 mg) was added and the mixture was stirred for 2.5 hours at 0° C. The reaction mixture was diluted with diethyl ether, washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride, dried with anhydrous sodium sulfate and concentrated under reduced pressure; the resulting residue was subjected to silica gel column chromatography (eluent; hexane/ethyl acetate=4/1) to give the titled compound (60 mg) as a pale yellow crystal.
Workup
- stirringthe mixture was stirred for 2.5 hours at 0° C
- washwashed with a saturated aqueous solution of sodium hydrogencarbonate
- dry with materiala saturated aqueous solution of sodium chloride, dried with anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-d22141500ad3430fab3eda7c6825004c
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06455708B1
Reaction notes
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