Imidazole → HCID 69019508, compound

HRID 860816Notes

Reaction equation

HRID 860816 reaction equation
Cl[CH:2]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)[C:3]1[CH:4]=[CH:5][C:6]2[NH:12][C:11](=[O:13])[CH2:10][N:9]=[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:7]=2[CH:20]=1.[NH:28]1[CH:32]=[CH:31][N:30]=[CH:29]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([CH:2]([N:28]2[CH:32]=[CH:31][N:30]=[CH:29]2)[C:3]2[CH:4]=[CH:5][C:6]3[NH:12][C:11](=[O:13])[CH2:10][N:9]=[C:8]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C:7]=3[CH:20]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 69019762HCID 69019762, compound

Product 1

HCID 69019508HCID 69019508, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of intermediate (29) (0.0125 mol), 1H-imidazole (0.0375 mol) and K2CO3 (8.62 g) in acetonitrile (150 ml) was stirred and refluxed for 3 h. The mixture was cooled, filtered off and the filtrate was evaporated till dryness. The residue was taken up in DCM. The organic layer was washed with water, dried (MgSO4), filtered off and evaporated. The residue (5.7 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97/3/0.1) (15–40 μm). The pure fractions were collected and evaporated. The residue (2.71 g) was crystallized from DIPE, yielding 2.38 g (51%) of (±)-7-[(4-chlorophenyl)-1H-imidazol-1-ylmethyl]-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one, mp. 144° C.

Workup

  1. temperaturerefluxed for 3 h
  2. temperatureThe mixture was cooled
  3. filtrationfiltered off
  4. customthe filtrate was evaporated till dryness
  5. washThe organic layer was washed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered off
  8. customevaporated
  9. customThe residue (5.7 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97/3/0.1) (15–40 μm)
  10. customThe pure fractions were collected
  11. customevaporated
  12. customThe residue (2.71 g) was crystallized from DIPE

Sources & evidence

ORD record
ord-5c68c7ecf31e465a928d0ae764b71bfd
Source dataset
uspto-grants-2006_12
Patent number
US07153958B2

Reaction notes

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