Benzene → N-(2-cyanoethyl)-2,2-bisfluoromethyl-6-trifluoromethyl-2H-1-benzopyran-4-carbothioamide

HRID 1067653Notes

Reaction equation

HRID 1067653 reaction equation
[C:1]([CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:13]2[CH:14]=[C:15]([C:18]([F:21])([F:20])[F:19])[CH:16]=[CH:17][C:12]=2[O:11][C:10]([CH2:24][F:25])([CH2:22][F:23])[CH:9]=1)=O)#[N:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:35])=CC=1.C1C=CC=CC=1>C(Cl)Cl>[C:1]([CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:13]2[CH:14]=[C:15]([C:18]([F:21])([F:20])[F:19])[CH:16]=[CH:17][C:12]=2[O:11][C:10]([CH2:24][F:25])([CH2:22][F:23])[CH:9]=1)=[S:35])#[N:2]

Participants

5

Reactant 3

HCID 241BenzeneHCID 87949Lawesson's reagentHCID 99507522,2-bis(fluoromethyl)-N-(2-cyanoethyl)-6-trifluoromethyl-2H-1-benzopyran-4-carboxamide

Product 1

HCID 18424394N-(2-cyanoethyl)-2,2-bisfluoromethyl-6-trifluoromethyl-2H-1-benzopyran-4-carbothioamideYield 89.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 92 mg of N-(2-cyanoethyl)-2,2-bisfluoromethyl-6-trifluorometyl-2H-1-benzopyran-4-carbamide, 60 mg of Lawesson's reagent and 2 ml of benzene was stirred with heating at 80° C. for one hour. The reaction mixture was subjected to silica gel column chromatography (eluent:methylene chloride) to give 50 mg of N-(2-cyanoethyl)-2,2-bisfluoromethyl-6-trifluoromethyl-2H-1-benzopyran-4-carbothioamide; m.p. 105-106° C.

Sources & evidence

ORD record
ord-078aa06b3a21443998989cc5ffe860f0
Source dataset
uspto-grants-2001_06
Patent number
US06248777B1

Reaction notes

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