5-Amino-3,4-dimethylisoxazole → N-(3,4-dimethyl-5-isoxazolyl)-2-(carbomethoxy)thiophene-3-sulfonamide

HRID 234312

반응식

HRID 234312 반응식
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[S:10](Cl)(=[O:12])=[O:11])=[O:4].[NH2:14][C:15]1[O:19][N:18]=[C:17]([CH3:20])[C:16]=1[CH3:21]>N1C=CC=CC=1>[CH3:20][C:17]1[C:16]([CH3:21])=[C:15]([NH:14][S:10]([C:9]2[CH:8]=[CH:7][S:6][C:5]=2[C:3]([O:2][CH3:1])=[O:4])(=[O:12])=[O:11])[O:19][N:18]=1

참가 물질

4

반응물 2

HCID 883175-Amino-3,4-dimethylisoxazoleHCID 27367332-Thiophenecarboxylic acid, 3-(chlorosulfonyl)-, methyl ester

생성물 1

HCID 10615322N-(3,4-dimethyl-5-isoxazolyl)-2-(carbomethoxy)thiophene-3-sulfonamide수율 65%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

2-Methoxycarbonylthiophene-3-sulfonyl chloride (2.50 g, 10.05 mmol) was added to a solution of 5-amino-3,4-dimethylisoxazole(0.98 g, 8.75 mmol) in dry pyridine (5.0 ml). The reaction mixture was stirred at room temperature for 16 h. Pyridine was removed under reduced pressure and the residue was partitioned between water and dichloromethane. The organic layer was washed with 1N HCl (2×50 ml) and dried over anhydrous magnesium sulfate. Evaporation of the solvents left an oily residue, which, after purification by column chromatography over silica gel (1:1 hexanes/ethyl acetate as eluent), yielded 2.20 mg (65%) of a brown solid. Further purification was achieved by recrystallization from ethyl acetate/hexanes, giving the pure product as a white solid, m.p. 113°-116° C.

후처리

  1. customPyridine was removed under reduced pressure
  2. customthe residue was partitioned between water and dichloromethane
  3. washThe organic layer was washed with 1N HCl (2×50 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customEvaporation of the solvents
  6. waitleft an oily residue, which
  7. customafter purification by column chromatography over silica gel (1:1 hexanes/ethyl acetate as eluent)

출처 및 근거

ORD 기록
ord-a980ca657da34400a5d38a3146522957
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05594021

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