Ethyl 2-chloroacetoacetate → HCID 23020202, compound

HRID 917386Notes

Reaction equation

HRID 917386 reaction equation
[CH:1]1([C:7]([NH2:9])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:19])=CC=1.Cl[CH:33]([C:39](=O)[CH3:40])[C:34]([O:36][CH2:37][CH3:38])=[O:35]>O1CCCC1>[CH:1]1([C:7]2[S:19][C:33]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[C:39]([CH3:40])[N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11858Ethyl 2-chloroacetoacetateHCID 14283CyclohexanecarboxamideHCID 87949Lawesson's reagent

Product 1

HCID 23020202HCID 23020202, compoundYield 184.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 90 ml of tetrahydrofuran, 11.1 g (87 mmol) of cyclohexanecarboxamide and 17.6 g (43.5 mmol) of Lawesson's reagent were suspended, followed by heating under refluxing for 3 hours. The reaction liquid was cooled to room temperature, followed by adding 14.4 g (87 mmol) of ethyl 2-chloro-3-oxobutanate and heating under refluxing for further 3 hours. The reaction liquid was poured into ice water and extracted with diethyl ether. The organic layer was washed with water, dilute hydrochloric acid, an aqueous solution of sodium carbonate and saturated saline solution in this order, followed by drying over anhydrous magnesium sulfate and concentrating under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:5) to obtain 20.3 g (yield: 92%) of ethyl 2-cyclohexyl-4-methylthiazole-5-carboxylate.

Workup

  1. temperatureby heating
  2. temperatureunder refluxing for 3 hours
  3. customThe reaction liquid
  4. temperatureheating
  5. temperatureunder refluxing for further 3 hours
  6. customThe reaction liquid
  7. extractionextracted with diethyl ether
  8. washThe organic layer was washed with water, dilute hydrochloric acid
  9. dry with materialby drying over anhydrous magnesium sulfate
  10. concentrationconcentrating under reduced pressure
  11. customThe residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:5)

Sources & evidence

ORD record
ord-9619eaddf1cb478fac706ff4ac2b0bbf
Source dataset
uspto-grants-2007_09
Patent number
US07273878B2

Reaction notes

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