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

HRID 2427266ノート

反応式

HRID 2427266 の反応式
[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]

参加物

3

反応物 1

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

生成物 1

HCID 12300671Ethyl 5-methylthiazole-4-carboxylate収率 68.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b5c31610baad4facb5551c2f4149a3cc
出典データセット
uspto-grants-2011_06
特許番号
US07968587B2

反応ノート

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