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

HRID 1429814노트

반응식

HRID 1429814 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
80 °C

실험 절차

A mixture of 7-(1-bromoethyl)-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.

후처리

  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

출처 및 근거

ORD 기록
ord-8d062d35247d4e5fba9ef7547620f3a0
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940752B2

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