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

HRID 474030
ノート
印刷プレビュー

反応式

HRID 474030 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) are charged to a flask fitted with reflux condenser. A solution of NaOH (3 eq., 50% aq.) is added and the mixture heated to 70° C. for 30-40 minutes. EtOAc was removed by distillation at 100 mm Hg and the mixture cooled to 5° C. The mixture was acidified with 6N HCl to pH 2. The solid is collected by vacuum filtration and washed with water (390 mL). The solid is taken up in CH2Cl2 (520 mL) and washed with saturated aqueous NaHCO3. The organic layer is dried over Na2SO4, filtered, and concentrated to give the desired material (174 g, 87%).

後処理

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

出典と根拠

ORDレコード
ord-f4e5b61026b64f0d88503e7232d47723
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08637511B2

反応ノート

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