2,5-Hexanedione → HCID 17964196, 화합물

HRID 1375022노트

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HRID 1375022 반응식
[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

참가 물질

5

반응물 3

HCID 80352,5-Hexanedione2회HCID 521998p-Toluenesulfonic acid monohydrate2회HCID 18952486151104-74-4

생성물 1

HCID 17964196HCID 17964196, 화합물

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

  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))

출처 및 근거

ORD 기록
ord-b0107006ae2046249ab636a33b6932e0
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07166598B2

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