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

HRID 4400

반응식

HRID 4400 반응식
[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

참가 물질

4

반응물 2

HCID 69484Ethyl 4-chloroacetoacetateHCID 12336049Cyclohexanecarbothioamide

생성물 1

HCID 15026349Ethyl 2-cyclohexyl-4-thiazoleacetate수율 71.3%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d744f03ba5db41d1bd7902f811b93a8d
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04725610

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