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

HRID 234312

反応式

HRID 234312 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a980ca657da34400a5d38a3146522957
出典データセット
uspto-grants-1997_01
特許番号
US05594021

関連ノート

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