Benzenesulfonyl chloride → HCID 66906833、化合物

HRID 57156ノート

反応式

HRID 57156 の反応式
Cl.[Br:2][C:3]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[S:5][C:4]=1[NH2:12].[C:13]1([S:19]([Cl:22])(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>N1C=CC=CC=1>[ClH:22].[Br:2][C:3]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[S:5][C:4]=1[NH:12][S:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:21])=[O:20]

参加物

4

反応物 2

HCID 7369Benzenesulfonyl chloride2 回HCID 66906974HCID 66906974、化合物

生成物 1

HCID 66906833HCID 66906833、化合物収率 36%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
50 °C

実験手順

To a solution of compound 145-H (0.46 g, 1.52 mmol) in pyridine (4.6 mL), cooled to 0° C., was added benzenesulfonyl chloride (0.206 mL, 1.60 mmol), and the reaction was heated to 50° C. for 72 h. Additional benzenesulfonyl chloride (0.412 mL, 3.20 mmol) was added and the reaction mixture was heated at 50° C. for an additional 16 h. The solvent was evaporated in vacuo, the residue dissolved in dichloromethane and washed with aqueous sodium bicarbonate. The aqueous layer was acidified with 1N HCl, extracted with dichloromethane, and the organic layer was evaporated in vacuo to afford a yellow solid (0.22 g, 36%) as a 1/3.5 mixture of the 3-bromo- and 3-chloro-substituted compounds, 145-Ia and 145-Ib, respectively. 1H-NMR (DMSO-d6): δ 7.1-7.2 (m, 1H), 7.4-7.6 (m, 3H), 7.8 (m, 2H), 8.1-8.2 (m, 1H), 8.25-8.35 (m, 1H); MS: m/z 465 and 509 (MH+).

後処理

  1. temperaturethe reaction mixture was heated at 50° C. for an additional 16 h
  2. customThe solvent was evaporated in vacuo
  3. dissolutionthe residue dissolved in dichloromethane
  4. washwashed with aqueous sodium bicarbonate
  5. extractionextracted with dichloromethane
  6. customthe organic layer was evaporated in vacuo

出典と根拠

ORDレコード
ord-83ab5dd2ade24808a966aa1072efd52c
出典データセット
uspto-grants-2016_09
特許番号
US09434711B2

反応ノート

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