3-Aminopropionitrile → 2,2-bis(fluoromethyl)-N-(2-cyanoethyl)-6-trifluoromethyl-2H-1-benzopyran-4-carboxamide

HRID 1067652Notes

Reaction equation

HRID 1067652 reaction equation
[F:1][CH2:2][C:3]1([CH2:20][F:21])[CH:8]=[C:7]([C:9](O)=[O:10])[C:6]2[CH:12]=[C:13]([C:16]([F:19])([F:18])[F:17])[CH:14]=[CH:15][C:5]=2[O:4]1.[C:22]([CH2:24][CH2:25][NH2:26])#[N:23]>O1CCCC1>[C:22]([CH2:24][CH2:25][NH:26][C:9]([C:7]1[C:6]2[CH:12]=[C:13]([C:16]([F:19])([F:18])[F:17])[CH:14]=[CH:15][C:5]=2[O:4][C:3]([CH2:2][F:1])([CH2:20][F:21])[CH:8]=1)=[O:10])#[N:23]

Participants

4

Reactant 2

HCID 16473-AminopropionitrileHCID 98796402,2-bis(fluoromethyl)-6-trifluoromethyl-2H-1-benzopyran-4-carboxylic acid

Product 1

HCID 99507522,2-bis(fluoromethyl)-N-(2-cyanoethyl)-6-trifluoromethyl-2H-1-benzopyran-4-carboxamideYield 85.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.20 g of 2,2-bisfluoromethyl-6-trifluoromethyl-2H-1-benzopyran-4-carboxylic acid, 0.12 g of N,N-carbonyl diimidazole and 3 ml of tetrahydrofuran was stirred at room temperature for one hour. The reaction mixture was combined with 0.06 g of 2-cyanoethylamine and further stirred at room temperature for 14 hours. The reaction mixture was concentrated under reduced pressure and the resulting residue was subjected to silica gel column chromatography (eluent; ethyl acetate:hexane=1:1) to give 0.20 g of N-(2-cyanoethyl)-2,2-bisfluoromethyl-6-trifluoromethyl-2H-1-benzopyran-4-carbamide; m.p. 135-136° C.

Workup

  1. stirringfurther stirred at room temperature for 14 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ca46cc77913e4d4ea4e2347ce190350d
Source dataset
uspto-grants-2001_06
Patent number
US06248777B1

Reaction notes

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