2,2'-Dithiodibenzoyl chloride → 3,3'-[Dithiobis(2,1-phenylenecarbonylimino)]bis-2-thiophenecarboxylic acid, dimethyl ester

HRID 3722

反応式

HRID 3722 の反応式
[C:1](Cl)(=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][S:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12](Cl)=[O:13].[NH2:21][C:22]1[CH:26]=[CH:25][S:24][C:23]=1[C:27]([O:29][CH3:30])=[O:28]>ClCCl.N1C=CC=CC=1>[C:11]1([C:12]([NH:21][C:22]2[CH:26]=[CH:25][S:24][C:23]=2[C:27]([O:29][CH3:30])=[O:28])=[O:13])[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=1[S:9][S:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:1]([NH:21][C:22]1[CH:26]=[CH:25][S:24][C:23]=1[C:27]([O:29][CH3:30])=[O:28])=[O:19]

参加物

5

反応物 2

HCID 881642,2'-Dithiodibenzoyl chlorideHCID 89652Methyl 3-amino-2-thiophenecarboxylate

生成物 1

HCID 867512593,3'-[Dithiobis(2,1-phenylenecarbonylimino)]bis-2-thiophenecarboxylic acid, dimethyl ester収率 59%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
23 °C

実験手順

A solution of 2,2'-dithiobisbenzoyl chloride (2.00 g, 5.83 mmol) in 50 mL of dichloromethane was added to a solution of methyl 3-amino-2-thiophenecarboxylate (1.82 g, 11.6 mmol) in 14 mL of pyridine at 23° C. The reaction mixture was stirred for 18 hours at 23° C. under nitrogen atmosphere. The precipitate formed was collected by filtration, then triturated with 5% aqueous HCl and washed with water to yield the crude product. The crude material was recrystallized first from ethanol, then from acetonitrile-DMF to yield 2.0 g of the title compound, mp 250°-252° C.

後処理

  1. customThe precipitate formed
  2. filtrationwas collected by filtration
  3. customtriturated with 5% aqueous HCl
  4. washwashed with water
  5. customto yield the crude product
  6. customThe crude material was recrystallized first from ethanol

出典と根拠

ORDレコード
ord-b718485e058f488da242388c9e90b503
出典データセット
uspto-grants-1998_03
特許番号
US05734081

関連ノート

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