N-bromobutanimide → 6-bromo-7-(1-bromoethyl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

HRID 58267ノート

反応式

HRID 58267 の反応式
[Br:1][CH:2]([C:4]1[N:5]=[C:6]2[S:13][CH:12]=[CH:11][N:7]2[C:8](=[O:10])[CH:9]=1)[CH3:3].[Br:14]N1C(=O)CCC1=O>C(#N)C>[Br:14][C:9]1[C:8](=[O:10])[N:7]2[CH:11]=[CH:12][S:13][C:6]2=[N:5][C:4]=1[CH:2]([Br:1])[CH3:3]

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 581114287-(1-bromoethyl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

生成物 1

HCID 581114456-bromo-7-(1-bromoethyl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one収率 16.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

A mixture of 7-(1-bromo ethyl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (17.5 g, 67.5 mmol) and N-bromosuccinimide (14.2 g, 79.8 mmol) in acetonitrile (400 mL) was stirred at 80° C. under N2 overnight. After removal of the solvent under reduced pressure, the resulting solid was dissolved in dichloromethane, washed sequentially with water, saturated aqueous Na2S2O3 and NaHCO3 solution and brine, dried over Na2SO4, and then concentrated to give crude product (3.7 g), which was used in the next step without further purification. LCMS calculated for C8H7Br2N2OS (M+H)+: m/z=336.9. Found: 336.9.

後処理

  1. customAfter removal of the solvent under reduced pressure
  2. dissolutionthe resulting solid was dissolved in dichloromethane
  3. washwashed sequentially with water, saturated aqueous Na2S2O3 and NaHCO3 solution and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-a7ca5a6fe12040b49c8e4c746c1c1b75
出典データセット
uspto-grants-2016_09
特許番号
US09434746B2

反応ノート

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