Ethyl 2-chloroacetoacetate → Ethyl 2-anilino-4-methyl-1,3-thiazole-5-carboxylate

HRID 642311

反応式

HRID 642311 の反応式
[C:1]1([NH:7][C:8]([NH2:10])=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:11]([O:13][C:14](=[O:20])[CH:15](Cl)[C:16](=O)[CH3:17])[CH3:12]>C(O)C>[CH2:11]([O:13][C:14]([C:15]1[S:9][C:8]([NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:10][C:16]=1[CH3:17])=[O:20])[CH3:12]

参加物

4

反応物 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 676454Phenylthiourea

生成物 1

HCID 807772Ethyl 2-anilino-4-methyl-1,3-thiazole-5-carboxylate収率 94.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of phenylthiourea (5.04 g, 33.1 mmol) and 2-chloro-3-oxo-butyric acid ethyl ester (4.8 mL, 34.8 mmol) in ethanol (50 mL) was refluxed for 19 h before it was cooled to room temperature and concentrated in vacuo. It was partitioned between ethyl acetate and saturated sodium bicarbonate, the organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a yellow solid (8.18 g): MS: (+) m/z 263.0 (M+1).

後処理

  1. temperaturewas refluxed for 19 h before it
  2. concentrationconcentrated in vacuo
  3. customIt was partitioned between ethyl acetate and saturated sodium bicarbonate
  4. washthe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-23aa6f1f39d544a784f68fdab31785e9
出典データセット
uspto-grants-2010_04
特許番号
US07696223B2

関連ノート

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