Dimethylformamide → HCID 178502018, compound

HRID 1761513Notes

Reaction equation

HRID 1761513 reaction equation
Br.Br[CH:3]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[C:4]1[CH:17]=[CH:16][C:7]2[NH:8][C:9]([NH:11][C:12](=[O:15])[O:13][CH3:14])=[N:10][C:6]=2[CH:5]=1.[CH3:25][C:26]1[NH:27][CH:28]=[CH:29][N:30]=1.CN(C)C=O>O>[F:24][C:21]1[CH:22]=[CH:23][C:18]([CH:3]([N:27]2[CH:28]=[CH:29][N:30]=[C:26]2[CH3:25])[C:4]2[CH:17]=[CH:16][C:7]3[NH:8][C:9]([NH:11][C:12](=[O:15])[O:13][CH3:14])=[N:10][C:6]=3[CH:5]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 127492-MethylimidazoleHCID 178419604HCID 178419604, compound

Product 1

HCID 178502018HCID 178502018, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 9.18 parts of methyl [5-[bromo(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]carbamate monohydrobromide, 12.3 parts of 2-methyl-1H-imidazole and 56.4 parts of N,N-dimethylformamide was stirred for 17 hours at room temperature. The reaction mixture was diluted with 300 parts of water. The precipitated product was filtered off and dissolved in dichloromethane. The organic layer was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane, methanol and methanol, saturated with ammonia, (90:5:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 27 parts of ethyl acetate. The product was filtered off, washed with 1,1'-oxybisethane and dried, yielding 2.6 parts (34.2%) of methyl [5-[(4-fluorophenyl)(2-methyl-1H-imidazol-1-yl)methyl]-1H-benzimidazol-2-yl]carbamate; mp. >300° C. (compound 6).

Workup

  1. filtrationThe precipitated product was filtered off
  2. dissolutiondissolved in dichloromethane
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane, methanol and methanol
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. customThe residue was crystallized from 27 parts of ethyl acetate
  11. filtrationThe product was filtered off
  12. washwashed with 1,1'-oxybisethane
  13. customdried

Sources & evidence

ORD record
ord-0caadf18b61a4089954f0ab8e4567f4d
Source dataset
uspto-grants-1989_05
Patent number
US04826862

Reaction notes

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