4-Toluenesulfonyl chloride → HCID 86608764、化合物

HRID 1959847ノート

反応式

HRID 1959847 の反応式
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([OH:23])=[C:11]([C:14]2[S:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)[C:12]#[N:13])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(N(CC)CC)C.[S:31](Cl)([C:34]1[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=1)(=[O:33])=[O:32]>ClCCl>[C:1]([N:4]1[CH2:5][CH2:6][CH:7]([C:10]([O:23][S:31]([C:34]2[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=2)(=[O:33])=[O:32])=[C:11]([C:14]2[S:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)[C:12]#[N:13])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 1363358063-(1-Acetylpiperidin-4-yl)-2-benzothiazol-2-yl-3-hydroxyacrylonitrile

生成物 1

HCID 86608764HCID 86608764、化合物収率 23%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of the above prepared 3-(1-acetylpiperidin-4-yl)-2-benzothiazol-2-yl-3-hydroxyacrylonitrile (415 mg, 1.27 mmol) in anhydrous dichloromethane (20 mL) at room temperature under argon were added triethylamine (193 mg, 1.9 mmol) and tosyl chloride (303 mg, 1.59 mmol) in small portions. The resulting mixture was stirred at room temperature for 6 hrs. The reaction mixture was diluted with dichloromethane. The organic phase was washed with 1% HCl, 0.5% NaOH, water, brine, and dried over anhydrous sodium sulfate, filtered, and evaporated. The resulting crude product was purified by flash column chromatography eluting with CH2Cl2:MeOH=20:1 to yield 140 mg (23%) of toluene-4-sulfonic acid 1-(1-acetylpiperidin-4-yl)-2-benzothiazol-2-yl-2-cyanovinyl ester. MS (m/z, ES+): 482.1 (M+1, 100%).

後処理

  1. washThe organic phase was washed with 1% HCl, 0.5% NaOH, water, brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe resulting crude product was purified by flash column chromatography
  6. washeluting with CH2Cl2

出典と根拠

ORDレコード
ord-78d8ba3d5ccd414789ce64681bf1434c
出典データセット
uspto-grants-2013_04
特許番号
US08410272B2

反応ノート

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