Diethyl phenylmalonate → HCID 178422335, compound

HRID 1851211Notes

Reaction equation

HRID 1851211 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 was stirred at 185° C. over night. After cooling to room temperature the reaction mixture forms two layers. 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-999229fcaf8343048a78307d68022c02
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

Loading…