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

HRID 383944

反応式

HRID 383944 の反応式
[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]

参加物

5

反応物 3

HCID 67184N-bromobutanimide2 回HCID 293353Ethyl 2-methyl-1,3-thiazole-4-carboxylateHCID 516892Sodium Bicarbonate

生成物 1

HCID 59291239Ethyl 5-bromo-2-methylthiazole-4-carboxylate収率 40.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a8c009059a5f495dae254bba06320339
出典データセット
uspto-grants-2013_02
特許番号
US08367696B2

関連ノート

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