Ethyl 2-amino-5-methylthiazole-4-carboxylate → Ethyl 5-methylthiazole-4-carboxylate

HRID 2427266노트

반응식

HRID 2427266 반응식
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8](N)[S:9][C:10]=1[CH3:11])=[O:5])[CH3:2]>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][S:9][C:10]=1[CH3:11])=[O:5])[CH3:2]

참가 물질

3

반응물 1

HCID 766578Ethyl 2-amino-5-methylthiazole-4-carboxylate

생성물 1

HCID 12300671Ethyl 5-methylthiazole-4-carboxylate수율 68.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

In a 3-neck round bottom flask mix 2-amino-5-methyl-thiazole-4-carboxylic acid ethyl ester (62.9 g, 338 mmol) and THF (630 mL). Heat to reflux and treat the reaction mixture with isoamyl nitrile (52.6 g, 60.1 mL, 449 mmol) dropwise. Upon completion of the addition, stir the reaction at reflux for 1 h, then concentrate the reaction mixture by rotavap (hi-vac) to give 70 g crude product as a thick orange oil. Purify on silica gel (400 g, 20-45% EtOAc/hexanes) to afford 39.47 g (68%) of the title compound as a yellow solid. LC-ES/MS m/z 172 (M+1), TR=1.5 min.

후처리

  1. temperatureHeat
  2. temperatureto reflux
  3. additionUpon completion of the addition
  4. customthe reaction
  5. temperatureat reflux for 1 h
  6. concentrationconcentrate the reaction mixture by rotavap (hi-vac)
  7. customto give 70 g crude product as a thick orange oil
  8. customPurify on silica gel (400 g, 20-45% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-b5c31610baad4facb5551c2f4149a3cc
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07968587B2

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