N-bromobutanimide → Ethyl 5-bromo-2-methylthiazole-4-carboxylate

HRID 383944

반응식

HRID 383944 반응식
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.C1C(=O)N([Br:19])C(=O)C1.C([O-])(O)=O.[Na+]>CC#N>[Br:19][C:4]1[S:3][C:2]([CH3:1])=[N:6][C:5]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

참가 물질

5

반응물 3

HCID 67184N-bromobutanimide2회HCID 293353Ethyl 2-methyl-1,3-thiazole-4-carboxylateHCID 516892Sodium Bicarbonate

생성물 1

HCID 59291239Ethyl 5-bromo-2-methylthiazole-4-carboxylate수율 40.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of ethyl 2-methyl-1,3-thiazole-4-carboxylate (14.53 g) in MeCN (150 mL) was added NBS (22.66 g), followed by heating under reflux for 3 hours. To the reaction mixture was added NBS (7.55 g), followed by heating under reflux for 2 hours. Under ice-cooling, to the reaction mixture was added a saturated aqueous NaHCO3 solution, followed by stirring for 5 minutes, and then extraction with EtOAc. The organic layer was dried over MgSO4 and then concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (hexane:EtOAc=from 100:0 to 60:40) to obtain ethyl 5-bromo-2-methyl-1,3-thiazole-4-carboxylate (8.52 g) as a yellow solid.

후처리

  1. temperatureby heating
  2. temperatureunder reflux for 3 hours
  3. temperatureby heating
  4. temperatureunder reflux for 2 hours
  5. temperatureUnder ice-cooling, to the reaction mixture
  6. extractionextraction with EtOAc
  7. dry with materialThe organic layer was dried over MgSO4
  8. concentrationconcentrated under reduced pressure
  9. customThe residue obtained
  10. customwas purified by silica gel column chromatography (hexane:EtOAc=from 100:0 to 60:40)

출처 및 근거

ORD 기록
ord-a8c009059a5f495dae254bba06320339
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367696B2

연결된 노트

불러오는 중…