Oxalyl chloride → 8-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid (2-chloro-phenyl)-amide

HRID 84592

反応式

HRID 84592 の反応式
[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6]3[N:7]=[C:8]([C:14]([OH:16])=O)[S:9][C:10]=3[CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1.[C:19]([Cl:24])(=O)[C:20](Cl)=O>ClCCl.CN(C=O)C>[Cl:24][C:19]1[CH:20]=[CH:3][CH:4]=[CH:5][C:6]=1[NH:7][C:14]([C:8]1[S:9][C:10]2[CH2:11][CH2:12][O:13][C:4]3[CH:3]=[C:2]([Br:1])[CH:18]=[CH:17][C:5]=3[C:6]=2[N:7]=1)=[O:16]

参加物

5

反応物 2

HCID 65578Oxalyl chlorideHCID 579001668-Bromo-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylic acid

生成物 1

HCID 668689618-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid (2-chloro-phenyl)-amide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

To a suspension of 8-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid (396 mg) in dry dichloromethane (20 mL) was added oxalyl chloride (180 μL) and DMF (1 drop). After 3 hours the solvent was removed in vacuo and to the residue was added acetonitrile (20 mL), 2-chloroaniline (140 μL) and sodium bicarbonate (111 mg). After 3 hours, water was added to the reaction mixture and the resulting precipitate was collected by filtration to yield 8-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid (2-chloro-phenyl)-amide (467 mg).

後処理

  1. customAfter 3 hours the solvent was removed in vacuo and to the residue
  2. additionwas added acetonitrile (20 mL), 2-chloroaniline (140 μL) and sodium bicarbonate (111 mg)
  3. additionwater was added to the reaction mixture
  4. filtrationthe resulting precipitate was collected by filtration

出典と根拠

ORDレコード
ord-2799d89860f043c6986f7ef290ffac7c
出典データセット
uspto-grants-2014_09
特許番号
US08846762B2

関連ノート

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