Ethyl 2-chloroacetoacetate → HCID 22628040, compound

HRID 278574Notes

Reaction equation

HRID 278574 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([NH2:15])=[S:14])=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[CH:19]([C:25]([CH3:27])=O)[C:20]([O:22][CH2:23][CH3:24])=[O:21].C([O-])(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(O)C.O>[C:1]([O:5][C:6]([NH:8][C:9]1[N:10]=[CH:11][C:12]([C:13]2[S:14][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:25]([CH3:27])[N:15]=2)=[CH:16][CH:17]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 11858Ethyl 2-chloroacetoacetateHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 22628074HCID 22628074, compound

Product 1

HCID 22628040HCID 22628040, compoundYield 27.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 6-tert-butoxycarbonylaminothionicotinamide (506 mg), ethyl 2-chloro-acetoacetate (492 mg) and sodium acetate (252 mg) in ethanol (20 ml) was heated for 2 hours under reflux, and to the mixture were added sodium hydrogen carbonate aqueous solution and water. The precipitated crystals were collected by filtration, and the crystals were successively washed with water, ethanol and ether to give ethyl 2-(6-tert-butoxycarbonylamino-3-pyridyl)-4-methyl-5-thiazolecarboxylate (200 mg).

Workup

  1. temperaturewas heated for 2 hours
  2. temperatureunder reflux
  3. filtrationThe precipitated crystals were collected by filtration
  4. washthe crystals were successively washed with water, ethanol and ether

Sources & evidence

ORD record
ord-e9a1a2104e924ef6879c487839e2e273
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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