Methyl iodide → HCID 14991004, compound

HRID 2248346Notes

Reaction equation

HRID 2248346 reaction equation
[N:1]1([CH2:6][C:7]2[CH:16]=[CH:15][C:10]3[N:11]([OH:14])[N:12]=[N:13][C:9]=3[CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[H][H].I[CH3:22]>CN(C)C=O>[N:1]1([CH2:6][C:7]2[CH:16]=[CH:15][C:10]3[N:11]([O:14][CH3:22])[N:12]=[N:13][C:9]=3[CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14990938HCID 14990938, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14991004HCID 14991004, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 4.5 parts of 5-(1H-imidazol-1-ylmethyl)-1H-benzotriazol-1-ol and 94 parts of N,N-dimethylformamide was added portionwise 1 part of a sodium hydride dispersion 50%. Upon complete addition, stirring was continued till hydrogen evolution had ceased. 1.3 Parts of iodomethane were added at once and stirring was continued at room temperature. The N,N-dimethylformamide formamide layer was evaporated and the residue was taken up in water and a mixture of trichloromethane, methanol and methanol, saturated with ammonia (90:5:5 by volume). The product was extracted with a mixture of trichloromethane, methanol and methanol, saturated with ammonia (90:5:5 by volume). The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel first using trichloromethane and then a mixture of trichloromethane and methanol (90:10 by volume) as eluents. The pure fractions were collected and the eluent was evaporated. The residue was stirred in 2,2'-oxybispropane. The product was filtered off and dried in vacuo at 50° C., yielding 3.1 parts (64.3%) of 5-(1H-imidazol-1-ylmethyl)-1-methoxy-1H-benzotriazole; mp. 94.3° C. (compound 221).

Workup

  1. additionUpon complete addition
  2. stirringstirring
  3. customwas continued at room temperature
  4. customThe N,N-dimethylformamide formamide layer was evaporated
  5. additiona mixture of trichloromethane, methanol and methanol
  6. extractionThe product was extracted with a mixture of trichloromethane, methanol and methanol, saturated with ammonia (90:5:5 by volume)
  7. customThe extract was dried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by column chromatography over silica gel first using trichloromethane
  11. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluents
  12. customThe pure fractions were collected
  13. customthe eluent was evaporated
  14. stirringThe residue was stirred in 2,2'-oxybispropane
  15. filtrationThe product was filtered off
  16. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-bbcd60a33f5c4258b68febef83faea2c
Source dataset
uspto-grants-1991_08
Patent number
US05039677

Reaction notes

Loading…