2,5-Hexanedione → HCID 17964196、化合物

HRID 1375022ノート

反応式

HRID 1375022 の反応式
[S:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])(=[O:3])[NH2:2].[CH3:18][C:19](=O)[CH2:20][CH2:21][C:22](=O)[CH3:23].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:23][C:22]1[N:2]([S:1]([C:5]2[CH:6]=[C:7]([CH:11]=[C:12]([C:14]([F:16])([F:15])[F:17])[CH:13]=2)[C:8]([OH:10])=[O:9])(=[O:3])=[O:4])[C:19]([CH3:18])=[CH:20][CH:21]=1

参加物

5

反応物 3

HCID 80352,5-Hexanedione2 回HCID 521998p-Toluenesulfonic acid monohydrate2 回HCID 18952486151104-74-4

生成物 1

HCID 17964196HCID 17964196、化合物

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 3-sulfamoyl-5-(trifluoromethyl)benzoic acid (200 mg) and 2,5-hexanedione (0.26 ml) in toluene (1 ml) was added p-toluenesulfonic acid monohydrate (28 mg), and the mixture was stirred under reflux with Dean-Stark Trap for 24 hours. Then 2,5-hexanedione (0.26 ml) and p-toluenesulfonic acid monohydrate (30 mg) was added to the mixture, and the mixture was stirred under the same condition for 24 hours. The mixture was evaporated and purified with column chromatography (silica gel, 50 ml, methanol:dichloromethane (5:95–20:80)) to give 3-[(2,5-dimethylpyrrol-1-yl)-sulfonyl]-5-(trifluoromethyl)benzoic acid (280 mg) as a crude solid. The solid was dissolved in a mixture of 1N sodium hydroxide aqueous solution (10 ml) and water (20 ml), and then adjusted to pH 1–2 with 1N hydrochloric acid (20 ml). The resulting powder was collected by filtration and dried under reduced pressure to give pure product (191.1 mg).

後処理

  1. temperatureunder reflux with Dean-Stark Trap for 24 hours
  2. stirringthe mixture was stirred under the same condition for 24 hours
  3. customThe mixture was evaporated
  4. custompurified with column chromatography (silica gel, 50 ml, methanol:dichloromethane (5:95–20:80))

出典と根拠

ORDレコード
ord-b0107006ae2046249ab636a33b6932e0
出典データセット
uspto-grants-2007_01
特許番号
US07166598B2

反応ノート

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