Diethyl phenylmalonate → HCID 178517335, compound

HRID 1915545Notes

Reaction equation

HRID 1915545 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][NH:4][N:3]=1.[C:7]1([CH:13]([C:19](OCC)=[O:20])[C:14](OCC)=[O:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(N(CCCC)CCCC)CCC>[C:7]1([C:13]2[C:14]([OH:15])=[N:1][C:2]3[N:3]([N:4]=[CH:5][CH:6]=3)[C:19]=2[OH:20])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 66514Diethyl phenylmalonateHCID 178418806HCID 178418806, compound

Product 1

HCID 178517335HCID 178517335, compound

Reagents, catalysts & solvents 1

HCID 7622TributylamineSolvent

Procedure

A solution of 9 g 3-amino pyrazole and 25.6 g diethyl phenylmalonate in N,N-dibutylbutan-1-amine is stirred at 185° C. over night. The reaction mixture consists of two layers after cooling to room temperature. 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-e0410bf2e0964f20a36f300df669b09f
Source dataset
uspto-grants-2013_12
Patent number
US08614218B2

Reaction notes

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