Methyl 4-chloroacetoacetate → HCID 178500938, compound

HRID 1725387Notes

Reaction equation

HRID 1725387 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 (153 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-c2eabf453e7f4e99842cda2fb6efb2c7
Source dataset
uspto-grants-2009_02
Patent number
US07491716B2

Reaction notes

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