3-Aminopropionitrile → N-(2-cyanoethyl)-2,2-bisfluoromethyl-6-trifluoromethyl-2H-1-benzopyran-4-carbothioamide
Reaction equation
[F:1][CH2:2][C:3]1([CH2:21][F:22])[CH:8]=[C:7]([C:9](=[S:12])OC)[C:6]2[CH:13]=[C:14]([C:17]([F:20])([F:19])[F:18])[CH:15]=[CH:16][C:5]=2[O:4]1.C1CC[N:31]2C(=[N:27][CH2:28][CH2:29][CH2:30]2)CC1.NCCC#N.C(OCC)(=O)C>O1CCCC1>[C:28]([CH2:29][CH2:30][NH:31][C:9]([C:7]1[C:6]2[CH:13]=[C:14]([C:17]([F:20])([F:19])[F:18])[CH:15]=[CH:16][C:5]=2[O:4][C:3]([CH2:21][F:22])([CH2:2][F:1])[CH:8]=1)=[S:12])#[N:27]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
O-methyl 2,2-bis(fluoromethyl)-6-trifluoromethyl-2H-1-benzopyran-4-carbothioate (0.34 g) and DBU (10 mg) were dissolved in tetrahydrofuran (5 ml); to the solution, 3-aminopropionitrile (0.2 ml) was added at room temperature in a nitrogen atmosphere and the resulting mixture was stirred for 7 hours at room temperature. Ethyl acetate was added to the reaction mixture, which was washed with water, dilute HCl, aqueous sodium bicarbonate and a saturated aqueous solution of sodium chloride. The mixture was dried with anhydrous sodium sulfate and concentrated under reduced pressure; the resulting residue was subjected to silica gel column chromatography (eluent; methylene chloride) to give the titled compound (0.33 g), which was identical to the authentic sample.
Workup
- washwas washed with water, dilute HCl, aqueous sodium bicarbonate
- dry with materialThe mixture was dried with anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-4f27571d20074e5981448aa2a898ef4b
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06455708B1
Reaction notes
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