2-Chlorocyclohexanone → 40639-93-8

HRID 1844979Notes

Reaction equation

HRID 1844979 reaction equation
Cl[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=O.[C:9]([NH:12][C:13]([NH2:15])=[NH:14])(=[O:11])[CH3:10]>CC#N>[NH:14]1[C:3]2[CH2:4][CH2:5][CH2:6][CH2:7][C:2]=2[N:15]=[C:13]1[NH:12][C:9](=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 132032-ChlorocyclohexanoneHCID 178475102HCID 178475102, compound

Product 1

HCID 1181961540639-93-8Yield 14.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5 g (38 mmol) of 2-chloro-cyclohexanone in MeCN (150 mL) was added 7 g (69 mmol) of N-acetyl-guanidine. The mixture was refluxed for 24 h. After removal of all the solvent, the residue was stirred with sat. aq. Na2CO3 (50 mL) for 5 min, filtered, and the solid was dried to provide 1 g (14%) of N-(4,5,6,7-tetrahydro-1H-benzoimidazol-2-yl)-acetamide. LCMS: 180 (M+1)+. 1H NMR (DMSO-d6, 400 MHz): δ 2.38 (m, 4H), 2.00(s, 3H), 1.65 (m, 4H) ppm.

Workup

  1. temperatureThe mixture was refluxed for 24 h
  2. customAfter removal of all the solvent
  3. filtrationfiltered
  4. customthe solid was dried

Sources & evidence

ORD record
ord-e6c8c58418e94a15b1b288e2e6b83f6a
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

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