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Ethyl Acetate → 2-chloro-N-(4-mercaptophenyl)benzamide

HRID 1162158
ノート
印刷プレビュー

反応式

HRID 1162158 の反応式
ClC1C=CC=CC=1C(=O)[S:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:21])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])=[CH:8][CH:7]=1.CCOC(C)=O.[OH-].[Na+]>O>[Cl:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:13]([NH:12][C:9]1[CH:10]=[CH:11][C:6]([SH:5])=[CH:7][CH:8]=1)=[O:21]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 59520030S-4-(2-chlorobenzamido)phenyl 2-chlorobenzothioate

生成物 1

HCID 271374192-chloro-N-(4-mercaptophenyl)benzamide収率 87%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

S-4-(2-chlorobenzamido)phenyl 2-chlorobenzothioate (305 g, 0.76 mol), EtOAc (325 mL), and water (65 mL) were charged to a flask fitted with a reflux condenser. A solution of NaOH (3 eq., 50% aq.) was added and the mixture heated to 70° C. for 30-40 minutes. EtOAc was removed by distillation at 100 mm Hg and the mixture was cooled to 5° C. The mixture was acidified with 6N HCl to pH 2. The solid was then collected by vacuum filtration and washed with water (390 mL). The solid was taken up in CH2Cl2 (520 mL) and washed with saturated aqueous NaHCO3. The organic layer was dried over Na2SO4, filtered, and concentrated to give the desired material (174 g, 87%).

後処理

  1. customfitted with a reflux condenser
  2. customEtOAc was removed by distillation at 100 mm Hg
  3. temperaturethe mixture was cooled to 5° C
  4. filtrationThe solid was then collected by vacuum filtration
  5. washwashed with water (390 mL)
  6. washwashed with saturated aqueous NaHCO3
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-a3b16339c90c4cb3972ef0d67d723db3
出典データセット
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07820685B2

反応ノート

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