Diethyl phenylmalonate → HCID 178517387, compound

HRID 2362153Notes

Reaction equation

HRID 2362153 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([NH2:6])=[N:2]1.C([O:9][C:10](=O)[CH:11]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:12](OCC)=[O:13])C>C(N(CCCC)CCCC)CCC>[C:17]1([C:11]2[C:10]([OH:9])=[N:6][C:3]3[N:2]([N:1]=[CH:5][N:4]=3)[C:12]=2[OH:13])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 66514Diethyl phenylmalonateHCID 178418311HCID 178418311, compound

Product 1

HCID 178517387HCID 178517387, compound

Reagents, catalysts & solvents 1

HCID 7622TributylamineSolvent

Conditions

Temperature
185 °C

Procedure

A mixture of 1H-[1,2,4]Triazol-3-ylamine SM (500 mg, 5.95 mmol) and 2-Phenyl-malonic acid diethyl ester 3-1 (1.41 g, 5.95 mmol) in N,N-dibutylbutan-1-amine (5 mL) was stirred at 185° C. overnight. The mixture was partitioned with two layers after cooling to room temperature. The top layer was removed and the lower layer was washed with cold PE. 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 to afford compound 3-2.

Workup

  1. customThe mixture was partitioned with two layers
  2. temperatureafter cooling to room temperature
  3. customThe top layer was removed
  4. washthe lower layer was washed with cold PE
  5. concentrationThe resulting solution was concentrated
  6. extractionextracted with a mixture of diethyl ether and 10% w/w NaOH solution
  7. filtrationThe precipitated product was collected by filtration

Sources & evidence

ORD record
ord-f779ad6d4c3e40a6bed8bf02592bedd7
Source dataset
uspto-grants-2014_04
Patent number
US08691825B2

Reaction notes

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