Ethyl Acetate → Ethyl 2-amino-4-phenyl-1,3-thiazole-5-carboxylate

HRID 47676

反応式

HRID 47676 の反応式
Cl[CH:2]([C:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:16][C:17]([NH2:19])=[S:18].CCOC(C)=O>CCO>[NH2:19][C:17]1[S:18][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:16]=1

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 2723790ThioureaHCID 9855991Ethyl 2-chloro-3-oxo-3-phenylpropanoate

生成物 1

HCID 73239Ethyl 2-amino-4-phenyl-1,3-thiazole-5-carboxylate収率 89%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of ethyl 2-chloro-3-oxo-3-phenylpropanoate (9.73 mmol) and thiourea (9.73 mmol) in EtOH (25 mL) was heated at reflux overnight. The resulting mixture was concentrated in vacuo, neutralized with 18M-NH4OH, and extracted with CH2Cl2. The organic phase was washed with brine, dried over anhydrous sodium sulfate, and concentrated to afford a yellow solid that was washed with MeOH (3 mL) and dried to afford the product in 89% yield as a pale yellow solid. MH+=249.1, Rf=0.29 (Hexanes:EtOAc=1:1). MH+=249.1, retention time (LC-MS)=2.37 min.

後処理

  1. temperatureat reflux overnight
  2. concentrationThe resulting mixture was concentrated in vacuo
  3. extractionextracted with CH2Cl2
  4. washThe organic phase was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customto afford a yellow solid
  8. washthat was washed with MeOH (3 mL)
  9. customdried
  10. customto afford the product in 89% yield as a pale yellow solid

出典と根拠

ORDレコード
ord-9b649c6b66cb49de8ed772aff219a18b
出典データセット
uspto-grants-2004_03
特許番号
US06699860B2

関連ノート

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