2-Chlorocyclohexanone → 40639-93-8

HRID 415129Notes

Reaction equation

HRID 415129 reaction equation
[C:1]([NH:4][C:5]([NH2:7])=[NH:6])(=[O:3])[CH3:2].Cl[CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=O>C(#N)C>[NH:6]1[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:9]=2[N:7]=[C:5]1[NH:4][C:1](=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 132032-ChlorocyclohexanoneHCID 178475102HCID 178475102, compound

Product 1

HCID 1181961540639-93-8

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Acetylguanidine (1.516 g, 15 mmol, 3 equivalents, commercially available from Aldrich) was added to 2-chlorocyclohexanone (5 mmol, 1 equiv) in acetonitrile (30 ml). The reaction mixture was heated to reflux for 12 hours under argon. Upon cooling, it was evaporated to dryness and the residue washed with water, filtered and air-dried to give 0.13 g of N-(4,5,6,7-tetrahydro-1H-benzo[d]imidazol-2-yl)acetamide. 1H-NMR (400 MHz, DMSO-d6) 13.4 (bs, 1H), 10.31 (bs, 1H), 2.55 (m, 2H), 2.49 (m, 2H). 2.02 (s, 3H), 1.67 (m, 2H), 1.62 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-4afb007778714524b5d5335de2132be9
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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