Water → 1-Methyl-5-phenyl-1H-imidazol-2-ylamine

HRID 333920Notes

Reaction equation

HRID 333920 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=CC=C[N:4]=1.Br[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O.O.NN.O>C(#N)C>[CH3:1][N:2]1[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:10][N:4]=[C:3]1[NH2:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6259Phenacyl bromideHCID 24654Hydrazine hydrate (1:1)HCID 2657762-Methylaminopyrimidine

Product 1

HCID 11329271-Methyl-5-phenyl-1H-imidazol-2-ylamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
130 °C

Procedure

To a microwave vial containing a solution of N-methylpyrimidin-2-amine (90b, 290 mg, 2.7 mmol) in acetonitrile (5 mL) was added 2-bromo-1-phenylethanone (714 mg, 3.6 mmol). The vial was sealed and heated in a microwave reactor at 130° C. for 20 minutes and then cooled to room temperature. The reaction mixture was treated with hydrazine hydrate (0.65 mL, 13.3 mmol) and then heated in a microwave reactor at 100° C. for 5.0 minutes. The solution was poured into water and filtered the precipitate to give 1-methyl-5-phenyl-1H-imidazol-2-ylamine (90c).

Workup

  1. customThe vial was sealed
  2. temperaturecooled to room temperature
  3. temperatureheated in a microwave reactor at 100° C. for 5.0 minutes
  4. filtrationfiltered the precipitate

Sources & evidence

ORD record
ord-8b18fa0dffb940c2a8df8b703b40232e
Source dataset
uspto-grants-2014_11
Patent number
US08883793B2

Reaction notes

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