Diethyl phenylmalonate → HCID 178422335, compound

HRID 1915591Notes

Reaction equation

HRID 1915591 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([CH3:7])[CH:3]=1.[C:8]1([CH:14]([C:20](OCC)=[O:21])[C:15](OCC)=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(N(CCCC)CCCC)CCC>[CH3:7][C:4]1[CH:3]=[C:2]2[N:1]=[C:15]([OH:16])[C:14]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[C:20]([OH:21])[N:6]2[N:5]=1

Participants

4

Reactant 2

HCID 66514Diethyl phenylmalonateHCID 178418690HCID 178418690, compound

Product 1

HCID 178422335HCID 178422335, compound

Reagents, catalysts & solvents 1

HCID 7622TributylamineSolvent

Procedure

A solution of 4.5 g 5-amino-3-methylpyrazole and 12.2 ml diethyl phenylmalonate in N,N-dibutylbutan-1-amine is stirred at 185° C. over night. After cooling to room temperature the reaction mixture forms two layers. The top layer is removed and the lower layer is diluted with dichloromethane and methanol. The resulting solution is concentrated and extracted with a mixture of diethyl ether and 10% w/w NaOH solution. The organic layer is discarded and aqueous layer acidified with concentrated HCl. The precipitated product is collected by filtration.

Workup

  1. customThe top layer is removed
  2. additionthe lower layer is diluted with dichloromethane and methanol
  3. concentrationThe resulting solution is concentrated
  4. extractionextracted with a mixture of diethyl ether and 10% w/w NaOH solution
  5. filtrationThe precipitated product is collected by filtration

Sources & evidence

ORD record
ord-f8046eefcd6e49239cc1ec42b4ee26e5
Source dataset
uspto-grants-2013_12
Patent number
US08614218B2

Reaction notes

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