2-Aminoimidazole → HCID 178421927, compound

HRID 1851194Notes

Reaction equation

HRID 1851194 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH2:6].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]>CN(C=O)C.C(N(CCCC)CCCC)CCC.O.ClCCl>[CH3:21][C:8]1[N:1]2[CH:5]=[CH:4][N:3]=[C:2]2[N:6]=[C:10]([OH:11])[C:9]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 2

HCID 821402-AminoimidazoleHCID 95389Ethyl acetylphenylacetate

Product 1

HCID 178421927HCID 178421927, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 7622TributylamineSolvent

Conditions

Temperature
180 °C

Procedure

A solution of 3.8 g 1H-imidazol-2-ylamine and 6 g ethyl 3-oxo-2-phenylbutanoate was 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 was diluted with water and dichloromethane, the phases separated, the aqueous layer extracted twice with dichloromethane, the combined organic layers were dried over Na2SO4 and concentrated to give the crude product. The crude product was 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 were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c5892d30c9314182b4b8a289ce63bfc1
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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