Methyl 4-chloroacetoacetate → HCID 178500938, compound

HRID 910092Notes

Reaction equation

HRID 910092 reaction equation
CC(C)([O-])C.[K+].[NH:7]1[CH:11]=[N:10][C:9]([SH:12])=[N:8]1.Cl[CH2:14][C:15](=[O:21])[CH2:16][C:17]([O:19][CH3:20])=[O:18]>CN(C)C=O>[O:21]=[C:15]([CH2:14][S:12][C:9]1[N:10]=[CH:11][NH:7][N:8]=1)[CH2:16][C:17]([O:19][CH3:20])=[O:18]

Participants

5

Reactant 3

HCID 36240Methyl 4-chloroacetoacetateHCID 23665647Potassium tert-butoxideHCID 178527894HCID 178527894, compound

Product 1

HCID 178500938HCID 178500938, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Add dropwise potassium tert-butoxide (11.4 g, 101.8 mmol) in 30 ml N,N-dimethylformamide (30 ml) to a solution of [1,2,4]triazole-3-thiol (10.3 gm, 101.8 mmol) in N,N-dimethylformamide (50 ml). Add dropwise methyl 4-chloroacetoacetate (15.3 gm, 101.8 mmol) in N,N-dimethylformamide (15 ml) and stir for 3 hours. Concentrate under reduced pressure, dilute with ethyl acetate (500 ml), filter, and concentrate under reduced pressure. Subject the residue to silica gel chromatography to provide the desired compound (18.3 gm, 83%) as a yellow oil.

Workup

  1. concentrationConcentrate under reduced pressure
  2. additiondilute with ethyl acetate (500 ml)
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-571d5bdcdde94c9cabf357d8ba9b441d
Source dataset
uspto-grants-2011_09
Patent number
US08022065B2

Reaction notes

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