Dimethylformamide → HCID 178421927, compound

HRID 503748Notes

Reaction equation

HRID 503748 reaction equation
N1[CH:5]=[N:4][C:3]([NH2:6])=[N:2]1.O=[C:8]([CH3:21])[CH:9]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:10](OCC)=[O:11].[CH3:22]N(C=O)C>C(N(CCCC)CCCC)CCC.O.ClCCl>[CH3:21][C:8]1[N:6]2[CH:22]=[CH:5][N:4]=[C:3]2[N:2]=[C:10]([OH:11])[C:9]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 95389Ethyl acetylphenylacetateHCID 178418311HCID 178418311, compound

Product 1

HCID 178421927HCID 178421927, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 7622TributylamineSolvent

Conditions

Temperature
180 °C

Procedure

A solution of 3.8 g 1,2,4-triazol-3-amine and 6 g ethyl 3-oxo-2-phenylbutanoate is suspended in a mixture of 32 ml DMF and 32 ml N,N-dibutylbutan-1-amine and heated by microwave irradiation to 180° C. for 10 h. The reaction mixture is diluted with water and dichloromethane, the phases separated, the aqueous layer extracted twice with dichloromethane, the combined organic layers are dried over Na2SO4 and concentrated to give the crude product. The crude product is purified by column chromatography (silica gel, dichloromethane/methanol).

Workup

  1. customthe phases separated
  2. extractionthe aqueous layer extracted twice with dichloromethane
  3. dry with materialthe combined organic layers are dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-637348febe354317b72ed4226981a1e6
Source dataset
uspto-grants-2010_08
Patent number
US07776864B2

Reaction notes

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