Hydrochloric Acid → N-(3-acetyl-4-chlorophenyl)-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide

HRID 1500067ノート

反応式

HRID 1500067 の反応式
C(Cl)(=O)C(Cl)=O.[CH3:7][N:8]1[C:12]([C:13]([OH:15])=O)=[C:11]([C:16]([F:19])([F:18])[F:17])[C:10]([C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[F:22])=[N:9]1.N1C=CC=CC=1.[NH2:33][C:34]1[CH:35]=[CH:36][C:37]([Cl:43])=[C:38]([C:40](=[O:42])[CH3:41])[CH:39]=1.Cl>CN(C=O)C.ClCCl.C1COCC1>[C:40]([C:38]1[CH:39]=[C:34]([NH:33][C:13]([C:12]2[N:8]([CH3:7])[N:9]=[C:10]([C:20]([F:26])([F:25])[C:21]([F:24])([F:22])[F:23])[C:11]=2[C:16]([F:18])([F:17])[F:19])=[O:15])[CH:35]=[CH:36][C:37]=1[Cl:43])(=[O:42])[CH3:41]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 65578Oxalyl chlorideHCID 15019111-(5-amino-2-chlorophenyl)ethanoneHCID 866600921-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

生成物 1

HCID 89650518N-(3-acetyl-4-chlorophenyl)-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide収率 80%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
40 °C

実験手順

Oxalyl chloride (0.65 ml, 0.95 g, 7.5 mmol, 1.5 eq.) followed by DMF (3 drops) were added to 1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid (1.56 g, 5.00 mmol) in dichloromethane (20 ml), and the mixture was heated to 40° C. After 9 h at 40° C., the mixture was concentrated under reduced pressure, THF (20 ml) and pyridine (0.8 ml, 0.8 g, 2.0 eq.) were added, followed by 1-(5-amino-2-chlorophenyl)ethanone (0.85 g, 5.00 mmol, 1.0 eq.) in THF (5 ml). The mixture was left at room temperature for 2 d. HCl N aq. solution) was added, the mixture was extracted with ethyl acetate and the extract was washed with HCl (1N aq. solution), NaOH ON aq. solution) and sat. aq. sodium chloride solution. The extract was dried over MgSO4 and, after concentration under reduced pressure, the product was purified by column chromatography on silica gel (hexane/ethyl acetate) to give N-(3-acetyl-4-chlorophenyl)-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (1.85 g, 80%).

後処理

  1. additionwere added
  2. waitThe mixture was left at room temperature for 2 d
  3. extractionthe mixture was extracted with ethyl acetate
  4. washthe extract was washed with HCl (1N aq. solution), NaOH ON aq. solution) and sat. aq. sodium chloride solution
  5. dry with materialThe extract was dried over MgSO4
  6. concentrationafter concentration under reduced pressure
  7. customthe product was purified by column chromatography on silica gel (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-327a6421a2b54688a812cde98fc6974b
出典データセット
uspto-grants-2015_12
特許番号
US09204645B2

反応ノート

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