N,N-Dimethylformamide--water (1/1) → HCID 136987057, compound

HRID 56052Notes

Reaction equation

[Cl:1][C:2]1[C:3]([CH:12]([N+:27]([O-])=[O:28])[CH2:13][NH:14][C:15](=[O:26])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([F:25])([F:24])[F:23])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.CN(C)C=O.O.N([O-])=O.[Na+]>O>[Cl:1][C:2]1[C:3]([C:12](=[N:27][OH:28])[CH2:13][NH:14][C:15](=[O:26])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([F:24])([F:25])[F:23])=[N:4][CH:5]=[C:6]([C:8]([F:9])([F:11])[F:10])[CH:7]=1

Participants

Conditions

Temperature: 47.5 °C

Procedure

To 19.80 g of N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-nitroethyl]-2-(trifluoromethyl)benzamide in 100 ml of a mixture of N,N-dimethylformamide-water (7:1), 21.65 g of sodium nitrite was added, and the mixture was stirred at from 45 to 50° C. for 12 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, poured into 150 ml of water and extracted with ethyl acetate (100 ml×2). The resulting organic layers were combined, washed with water (100 ml×1) and dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 3:7 to 1:1) as the eluent to obtain 11.10 g of the desired product as white crystals.

Workup

customAfter completion of the reaction
temperatureto cool to room temperature
extractionextracted with ethyl acetate (100 ml×2)
washwashed with water (100 ml×1)
dry with materialdried over saturated aqueous sodium chloride
customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-e5ecb3f27d5244bbbbc710000a05b692
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434684B2

Reaction notes

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