Dimethylformamide → 5-Bromopyrimidine-2-carbonyl chloride

HRID 1027699ノート

反応式

HRID 1027699 の反応式
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[Br:7][C:8]1[CH:9]=[N:10]C(C(O)=O)=[N:12][CH:13]=1.CN(C)C=O>ClCCl.CN(C)C=O.CO>[Br:7][C:8]1[CH:13]=[N:12][C:1]([C:2]([Cl:4])=[O:3])=[N:10][CH:9]=1

参加物

7

反応物 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 164629705-Bromopyrimidine-2-carboxylic acid

生成物 1

HCID 596746575-Bromopyrimidine-2-carbonyl chloride収率 100%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

Oxalyl chloride (47.4 g, 369 mmol) was added to a suspension of 5-Bromo-pyrimidine-2-carboxylic acid (50 g, 250 mmol) in dichloromethane (821 ml) at room temperature followed by 1-2 drop of dimethylformamide. The reaction mixture was stirred under nitrogen for 2 hours LCMS in methanol indicated the presence of the methyl ester and some acid. Dimethylformamide (0.2 ml) was added to the reaction mixture. The acid dissolved after 30 minutes. LCMS showed corresponding methyl ester and no starting material peak was observed. The solvent was removed and dried in vacuo to afford the crude 5-Bromo-pyrimidine-2-carbonyl chloride (55 g, 100%).

後処理

  1. dissolutionThe acid dissolved after 30 minutes
  2. customThe solvent was removed
  3. customdried in vacuo

出典と根拠

ORDレコード
ord-0996af05180240c29e39d7292b712f9e
出典データセット
uspto-grants-2014_05
特許番号
US08735396B2

反応ノート

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