Diisopropylethylamine → HCID 22998459、化合物

HRID 1166957ノート

反応式

HRID 1166957 の反応式
C(N(CC)C(C)C)(C)C.[CH3:10][C:11]1[C:15]([CH3:16])=[C:14]([NH:17][S:18]([C:21]2[CH:25]=[CH:24][S:23][CH:22]=2)(=[O:20])=[O:19])[O:13][N:12]=1.[CH3:26][Si:27]([CH3:34])([CH3:33])[CH2:28][CH2:29][O:30][CH2:31]Cl>C(Cl)Cl>[CH3:26][Si:27]([CH3:34])([CH3:33])[CH2:28][CH2:29][O:30][CH2:31][C:22]1[S:23][CH:24]=[CH:25][C:21]=1[S:18]([NH:17][C:14]1[O:13][N:12]=[C:11]([CH3:10])[C:15]=1[CH3:16])(=[O:19])=[O:20]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 22998511N-(3,4-dimethyl-5-isoxazolyl)thiophene-3-sulfonamide

生成物 1

HCID 22998459HCID 22998459、化合物収率 71.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

N,N-diisopropylethylamine (222 μl, 128 mmol) was added to a solution of N-(3,4-dimethyl-5-isoxazolyl)thiophene-3-sulfonamide (300 mg, 1.16 mmol) in methylene chloride (5 ml), and the mixture was stirred at room temperature for 15 min. The mixture was then cooled to 0° C. and 2-(trimethylsilyl)ethoxy methyl chloride (SEM chloride) (226 μl, 1.28 mmol) was added dropwise via syringe, and the resultant yellow solution was stirred at room temperature for 5 hours. Evaporation of solvents left an oil which was extracted into ethyl acetate, washed with water and brine solution and dried over magnesium sulfate. Flash chromatography of the residue using 10% ethyl acetate/hexanes yielded 321 mg 2-[2-(trimethylsilyl)ethoxymethyl]-N-(3,4-dimethyl-5-isoxazolyl)thiophene-3-sulfonamide as a clear colorless oil which solidified into a white solid upon standing (71% yield).

後処理

  1. temperatureThe mixture was then cooled to 0° C.
  2. stirringthe resultant yellow solution was stirred at room temperature for 5 hours
  3. customEvaporation of solvents
  4. waitleft an oil which
  5. extractionwas extracted into ethyl acetate
  6. washwashed with water and brine solution
  7. dry with materialdried over magnesium sulfate

出典と根拠

ORDレコード
ord-ec10c4d38f6747d79982900e0a17b4b4
出典データセット
uspto-grants-2003_09
特許番号
US06613804B2

反応ノート

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