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

HRID 1748324Notes

Reaction equation

HRID 1748324 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-ylamineYield 42%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
130 °C

Procedure

To a microwave vial containing a solution of N-methylpyrimidin-2-amine (290 mg, 2.7 mmol) in acetonitrile (5 mL) is added 2-bromo-1-phenylethanone (714 mg, 3.6 mmol). The vial is sealed and heated in a microwave reactor at 130° C. for 20 minutes and is cooled to room temperature. The mixture is treated with hydrazine hydrate (0.65 mL, 13.3 mmol) and is then heated in a microwave reactor at 100° C. for 5 minutes. The reaction is poured into water (30 mL) and filtered to afford the title compound (192 mg, 42%) as a solid.

Workup

  1. customThe vial is sealed
  2. temperatureis cooled to room temperature
  3. temperatureis then heated in a microwave reactor at 100° C. for 5 minutes
  4. filtrationfiltered

Sources & evidence

ORD record
ord-20e88d400cb54887ad9f0d7f196b5f93
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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