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

HRID 4400

Reaction equation

HRID 4400 reaction equation
[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

Participants

4

Reactant 2

HCID 69484Ethyl 4-chloroacetoacetateHCID 12336049Cyclohexanecarbothioamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-d744f03ba5db41d1bd7902f811b93a8d
Source dataset
uspto-grants-1988_02
Patent number
US04725610

Linked notes

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