Citric Acid → N-(4-Chlorophenyl)-3-methoxy-benzenesulfonamide

HRID 2079603

反応式

HRID 2079603 の反応式
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([S:17](Cl)(=[O:19])=[O:18])[CH:14]=[CH:15][CH:16]=1.N1C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl.O>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][S:17]([C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([O:10][CH3:9])[CH:12]=2)(=[O:19])=[O:18])=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 311Citric AcidHCID 1049PyridineHCID 78124-ChloroanilineHCID 27375043-Methoxybenzenesulfonyl chloride

生成物 1

HCID 57788151N-(4-Chlorophenyl)-3-methoxy-benzenesulfonamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

To a solution of 4-chloroaniline (400 mg, 3.13 mmol) in anhydrous dichloromethane (40 mL) were added 3-methoxybenzenesulfonyl chloride (648 mg, 3.13 mmol) followed by pyridine (297.2 mg, 3.76 mmol). The mixture was allowed to stir for 12 h at 25° C. 10% citric acid solution (20 mL) and water (20 mL) was added. The organic phase was dried (Na2SO4), and evaporated under reduced pressure yielding the title compound as solid which was used as such in the next step. Yield: 900 mg (96%). MS (m/e): 296 (M+−H); 1H-NMR (CDCl3, 400 MHz): δ 3.76 (s, 3H), 6.48 (brs, 1H), 7.0 (d, J=8.72 Hz, 2H), 7.06 (d, J=7.76 Hz, 1H), 7.21 (m, 3H), 7.32 (m, 2H).

後処理

  1. dry with materialThe organic phase was dried (Na2SO4)
  2. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-bf36f5f2bdfa42f99f69fd1332a065ac
出典データセット
uspto-grants-2011_04
特許番号
US07932269B2

関連ノート

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