1,1'-Carbonyldiimidazole → 2H-Benzimidazol-2-one, 6-chloro-1-(cyclohexylmethyl)-1,3-dihydro-

HRID 1081461Notes

Reaction equation

HRID 1081461 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH:9][CH2:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:3]=1.[C:17](N1C=CN=C1)(N1C=CN=C1)=[O:18]>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:17](=[O:18])[N:9]([CH2:10][CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]3)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 11207166HCID 11207166, compound

Product 1

HCID 52763842H-Benzimidazol-2-one, 6-chloro-1-(cyclohexylmethyl)-1,3-dihydro-Yield 70.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 7.2 g of the compound obtained in step B) and 6.7 g of 1,1'-carbonyldiimidazole in 100 ml of acetonitrile is refluxed for 5 minutes. The solvent is evaporated off under vacuum, the residue is taken up with water, extracted with DCM, washed with a saturated solution of NaHCO3 and dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using a DCM/MeOH mixture (95/5; v/v) as the eluent to give 5.6 g of the expected product. M.p.=173° C.

Workup

  1. temperatureis refluxed for 5 minutes
  2. customThe solvent is evaporated off under vacuum
  3. extractionextracted with DCM
  4. washwashed with a saturated solution of NaHCO3
  5. dry with materialdried over Na2SO4
  6. customthe solvent is evaporated off under vacuum
  7. customThe residue is chromatographed on silica using a DCM/MeOH mixture (95/5; v/v) as the eluent

Sources & evidence

ORD record
ord-4cbdb89795014332ba00b1470f51bede
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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