Dimethylformamide → HCID 58799476, 화합물

HRID 346813

반응식

HRID 346813 반응식
[CH3:1][N:2]1[CH:6]=[C:5]([C:7](O)=[O:8])[C:4]([C:10]([F:13])([F:12])[F:11])=[N:3]1.C(Cl)(=O)C(Cl)=O.CN(C=O)C.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[NH2:38])=[CH:28][CH:27]=1>C(Cl)Cl.C(N(CC)CC)C>[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[NH:38][C:7]([C:5]2[C:4]([C:10]([F:13])([F:12])[F:11])=[N:3][N:2]([CH3:1])[CH:6]=2)=[O:8])=[CH:30][CH:31]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 2622612-Amino-4'-chlorobiphenylHCID 27756651-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid

생성물 1

HCID 58799476HCID 58799476, 화합물수율 60.4%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8471Triethylamine용매

실험 절차

A solution of 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (0.68 g) and oxalyl chloride (0.49 g) in methylene chloride (30 ml) is stirred for 2 hours at room temperature in the presence of a catalytic amount of DMF. The resulting acid chloride solution is then added to a solution of 4′-chlorobiphenyl-2-ylamine (0.71 g) and triethylamine (0.36 g) in 15 ml of methylene chloride at 0° C. The reaction mixture is then stirred for 4 hours at room temperature. After distilling off the solvent in a water-jet-vacuum, the residue is taken up in ethylacetate/water. The ethylacetate phase is extracted twice with water. After drying of the organic phase with Na2SO4, the solvent is distilled off in a water-jet-vacuum and the residue purified by column chromatography (silica gel; eluant: ethylacetate/hexane=1:1). 0.8 g of 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (4′-chlorobiphenyl-2-yl) amide are obtained in the form of slightly brownish crystals having a melting point of 144–146° C.

후처리

  1. distillationAfter distilling off the solvent in a water-jet-vacuum
  2. extractionThe ethylacetate phase is extracted twice with water
  3. dry with materialAfter drying of the organic phase with Na2SO4
  4. distillationthe solvent is distilled off in a water-jet-vacuum
  5. customthe residue purified by column chromatography (silica gel; eluant: ethylacetate/hexane=1:1)

출처 및 근거

ORD 기록
ord-99ae9128fab0475badea545ca848a26e
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173055B1

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