Diethyl phenylmalonate → HCID 178517335, compound

HRID 1851189Notes

Reaction equation

HRID 1851189 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 was stirred at 185° C. over night. The reaction mixture consisted of two layers after cooling to room temperature. The top layer was removed and the lower layer was diluted with dichloromethane and methanol. The resulting solution was concentrated and extracted with a mixture of diethyl ether and 10% w/w NaOH solution. The organic layer was discarded and aqueous layer acidified with concentrated HCl. The precipitated product was collected by filtration.

Workup

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

Sources & evidence

ORD record
ord-8663bc00a8064f22bec8e2e6e8ec0ac3
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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