Aniline → 3-chloro-N-phenylbenzamide

HRID 872262

反応式

HRID 872262 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[Cl:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14](Cl)=[O:15]>C(Cl)Cl.O>[Cl:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:15]

参加物

6

反応物 3

HCID 6115AnilineHCID 14798Sodium HydroxideHCID 69252Benzoyl chloride, 3-chloro-

生成物 1

HCID 7223903-chloro-N-phenylbenzamide収率 81%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of aniline (178 mg, 1.9 mmol) in 20 mL CH2Cl2 at room temperature was added NaOH (76.2 mg, 2.9 mmol) in 6 mL water. This mixture was stirred vigorously for 5 minutes after which 3-chlorobenzoyl chloride (500 mg, 2.9 mmol) was added drop-wise while stirring over a period of 30 minutes. This reaction mixture was stirred for an additional 2 hours followed by an acid work-up and extraction with CH2Cl2 (3×20 mL). The organic layers were combined, dried over anhydrous MgSO4. The product was purified via column chromatography on silica gel and eluted with a CHCl3/MeOH/Et3N (9.8:0.1:0.1) to give white crystals in 81% yield.

後処理

  1. additionwas added drop-wise
  2. stirringThis reaction mixture was stirred for an additional 2 hours
  3. extractionfollowed by an acid work-up and extraction with CH2Cl2 (3×20 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. customThe product was purified via column chromatography on silica gel
  6. washeluted with a CHCl3/MeOH/Et3N (9.8:0.1:0.1)
  7. customto give white crystals in 81% yield

出典と根拠

ORDレコード
ord-c94a85ee94c949c89095fa3a5e421cf7
出典データセット
uspto-grants-2015_03
特許番号
US08975288B2

関連ノート

読み込み中…