Chloroacetone → HCID 178474451, compound

HRID 415046Notes

Reaction equation

HRID 415046 reaction equation
[C:1]([NH:4][C:5]([NH2:7])=[NH:6])(=[O:3])[CH3:2].Cl[CH2:9][C:10](=O)[CH3:11]>C(#N)C>[CH3:11][C:10]1[N:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[NH:7][CH:9]=1

Participants

4

Reactant 2

HCID 6571ChloroacetoneHCID 178475102HCID 178475102, compound

Product 1

HCID 178474451HCID 178474451, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Acetylguanidine (1.516 g, 15 mmol, 3 equivalents, commercially available Aldrich) was added to 1-chloropropan-2-one (0.462 g, 5 mmol, 1 equiv) in acetonitrile (30 ml). The reaction mixture was heated to reflux for 12 hours under argon. Upon cooling, the reaction mixture was evaporated to dryness and the isolated residue was washed with water, filtered and air-dried to give 0.324 g N-(4-methyl-1H-imidazol-2-yl)acetamide. 1H-NMR (400 MHz, DMSO-d6): δ 13.3 (bs, 1H), 10.29 (bs, 1H), 6.80 (s, 1H), 2.27 (s, 3H), 2.02 (s, 3).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 12 hours under argon
  3. temperatureUpon cooling
  4. customthe reaction mixture was evaporated to dryness
  5. washthe isolated residue was washed with water
  6. filtrationfiltered
  7. customair-dried

Sources & evidence

ORD record
ord-e66492094aa0491388b0c8d9d3ac4361
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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