Dimethylformamide → 5-methyl-1-[4-(trifluoromethyl)phenyl]-1H-pyrazole-4-carboxamide

HRID 1748633노트

반응식

HRID 1748633 반응식
C(Cl)(=O)C(Cl)=O.C[N:8](C)[CH:9]=[O:10].[CH3:12][C:13]1[N:17]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[N:16]=[CH:15][C:14]=1C(O)=O>ClCCl.O>[CH3:12][C:13]1[N:17]([C:18]2[CH:19]=[CH:20][C:21]([C:24]([F:27])([F:25])[F:26])=[CH:22][CH:23]=2)[N:16]=[CH:15][C:14]=1[C:9]([NH2:8])=[O:10]

참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 107784295-methyl-1-(4-(trifluoromethyl)phenyl)-1H-pyrazole-4-carboxylic acid

생성물 1

HCID 178227615-methyl-1-[4-(trifluoromethyl)phenyl]-1H-pyrazole-4-carboxamide

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

Oxalyl chloride (3.8 ml) and N,N-dimethylformamide (catalytic amounts) were added at room temperature to a solution of 5-methyl-1-[4-(trifluoromethyl)phenyl]-1H-pyrazole-4-carboxylic acid (3.0 g) described in Reference Example 23 in dichloromethane (50 ml) and stirred at room temperature for two hours. The solvent and an excess amount of oxalyl chloride were evaporated, tetrahydrofuran (50 ml) was added to the residue, 28% aqueous ammonia was added under ice-cooling, and stirred at room temperature for two hours. After the reaction, the reaction solution was diluted with water and extracted with ethyl acetate. The resulting organic layer was washed with 1N hydrochloric acid aqueous solution, 4N aqueous solution of sodium hydroxide, water and saturated brine successively, dried over anhydrous sodium sulfate and concentrated to give 5-methyl-1-[4-(trifluoromethyl)phenyl]-1H-pyrazole-4-carboxamide (2.92 g) as a pale brown solid.

후처리

  1. customThe solvent and an excess amount of oxalyl chloride were evaporated
  2. additiontetrahydrofuran (50 ml) was added to the residue, 28% aqueous ammonia
  3. additionwas added under ice-
  4. temperaturecooling
  5. stirringstirred at room temperature for two hours
  6. customAfter the reaction
  7. extractionextracted with ethyl acetate
  8. washThe resulting organic layer was washed with 1N hydrochloric acid aqueous solution, 4N aqueous solution of sodium hydroxide, water and saturated brine successively
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b94063d473de44b385e98b2f718fbb9c
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150555B2

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