Ethanol → HCID 14991011, compound

HRID 2166068Notes

Reaction equation

HRID 2166068 reaction equation
[N:1]1([CH2:6][C:7]2[CH:8]=[CH:9][C:10]3[N:14]=[N:13][N:12]([OH:15])[C:11]=3[CH:16]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[OH-].[Na+].[CH2:19](O)C>>[N:1]1([CH2:6][C:7]2[CH:8]=[CH:9][C:10]3[N:14]=[N:13][N:12]([O:15][CH3:19])[C:11]=3[CH:16]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 14990941HCID 14990941, compound

Product 1

HCID 14991011HCID 14991011, compoundYield 65.4%

Procedure

To a stirred suspension of 4.7 parts of 6-(1H-imidazol-1-ylmethyl)-1H-benzotriazol-1-ol in 60 parts of ethanol were added 22.5 parts of a sodium hydroxide solution 1N. The whole was stirred till a clear solution was obtained. The mixture was evaporated to dry. The residue was dissolved in 18 parts of N,N-dimethylformamide. To the thus obtained solution was added at once a solution of 3.2 parts of iodomethane in 9 parts of N,N-dimethylformamide. After stirring for 30 minutes at room temperature, the whole was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was recrystallized from 8 parts of 4-methyl-2-pentanone. The product was filtered off and dried, yielding 3.3 parts (65.4%) of 6-(1H-imidazol-1-ylmethyl)-1-methoxy-1H-benzotriazole; mp. 132.4° C. (compound 229).

Workup

  1. customwas obtained
  2. customThe mixture was evaporated
  3. customto dry
  4. dissolutionThe residue was dissolved in 18 parts of N,N-dimethylformamide
  5. additionTo the thus obtained solution was added at once a solution of 3.2 parts of iodomethane in 9 parts of N,N-dimethylformamide
  6. stirringAfter stirring for 30 minutes at room temperature
  7. customthe whole was evaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. customThe residue was recrystallized from 8 parts of 4-methyl-2-pentanone
  13. filtrationThe product was filtered off
  14. customdried

Sources & evidence

ORD record
ord-de1540034c134c8b96ac7f5f90532dd9
Source dataset
uspto-grants-1990_07
Patent number
US04943574

Reaction notes

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