Ethyl 4-chloroacetoacetate → Ethyl 2-cyclohexyl-4-thiazoleacetate

HRID 4400

反応式

HRID 4400 の反応式
[CH:1]1([C:7](=[S:9])[NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:11][C:12](=O)[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]>C(O)C>[CH:1]1([C:7]2[S:9][CH:11]=[C:12]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

4

反応物 2

HCID 69484Ethyl 4-chloroacetoacetateHCID 12336049Cyclohexanecarbothioamide

生成物 1

HCID 15026349Ethyl 2-cyclohexyl-4-thiazoleacetate収率 71.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of cyclohexanethiocarboxamide (5.0 g), ethyl 4-chloroacetoacetate (5.74 g), ethanol (50 ml) was heated under reflux for 1 hour. After dilution with water, mixture was extracted with ethyl acetate. The extract was washed with aqueous sodium bicarbonate solution and water, dried (MgSO4), and concentrated. The residue was purified by chromatography on silica gel with ethyl acetate-hexane (1:4) to yield ethyl 2-cyclohexyl-4-thiazoleacetate as an oil (6.3 g, 70.9%). IR (Neat): 1735, 1255 cm-1. NMR (CDCl3)δ: 1.28 (3H, t, J=7 Hz), 1.2-2.3 (10H, m), 2.97 (1H, m), 3.77 (2H, s), 4.17 (2H, q, J=7 Hz), 7.0 (1H, s).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. extractionAfter dilution with water, mixture was extracted with ethyl acetate
  4. washThe extract was washed with aqueous sodium bicarbonate solution and water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel with ethyl acetate-hexane (1:4)

出典と根拠

ORDレコード
ord-d744f03ba5db41d1bd7902f811b93a8d
出典データセット
uspto-grants-1988_02
特許番号
US04725610

関連ノート

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