m-Chloroperbenzoic acid → HCID 22057734、化合物

HRID 891261ノート

反応式

HRID 891261 の反応式
ClC1C=C(C=CC=1)C(OO)=[O:6].[N:12]1[CH:17]=[CH:16][C:15]([CH2:18][NH:19][C:20]2[CH:38]=[CH:37][CH:36]=[CH:35][C:21]=2[C:22]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=2)=[O:23])=[CH:14][CH:13]=1>ClCCl>[O-:6][N+:12]1[CH:17]=[CH:16][C:15]([CH2:18][NH:19][C:20]2[CH:38]=[CH:37][CH:36]=[CH:35][C:21]=2[C:22]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:32])([F:33])[F:34])[CH:26]=2)=[O:23])=[CH:14][CH:13]=1

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 63988832-((4-pyridyl)methyl)amino-N-(3-(trifluoromethyl)phenyl)benzamide

生成物 1

HCID 22057734HCID 22057734、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

3-Chloroperoxybenzoic acid (2.06 g of 70%, 8.4 mmol) is added to a stirred mixture of 2-[(4-pyridyl)methyl]amino-N-[3-(trifluoromethyl)phenyl]benzamide (Example 14; 1.86 g, 5 mmol) in dichloromethane (50 mL) at 0° C. The resulting mixture is then stirred at room temperature for 15 hours. The mixture is diluted with dichloromethane (100 mL) and washed sequentially with aqueous sodium hydroxide (2×100 mL) and aqueous sodium thiosulphate (2×50 mL of 10%). The organic phase is dried (Na2SO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by column chromatography on silica gel, eluent 20% ethanol in ethyl acetate, and recrystallised from ethyl acetate-hexane to give the title compound as a colourless crystalline solid, m.p. 181–184° C.

後処理

  1. washwashed sequentially with aqueous sodium hydroxide (2×100 mL) and aqueous sodium thiosulphate (2×50 mL of 10%)
  2. dry with materialThe organic phase is dried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent is evaporated off under reduced pressure
  5. customto yield the crude product which
  6. customis purified by column chromatography on silica gel, eluent 20% ethanol in ethyl acetate
  7. customrecrystallised from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-cc26beea760f45f98455040181ffbabc
出典データセット
uspto-grants-2006_02
特許番号
US07002022B2

反応ノート

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