Imidazole → 6-[(4-chlorophenyl)(1H-imidazol-1-yl)methyl]-1-methyl-1H-benzotriazole

HRID 2166056Notes

Reaction equation

HRID 2166056 reaction equation
Br.Br[CH:3]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[C:4]1[CH:5]=[CH:6][C:7]2[N:11]=[N:10][N:9]([CH3:12])[C:8]=2[CH:13]=1.[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1>CC1C=CC=CC=1>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([CH:3]([N:21]2[CH:25]=[CH:24][N:23]=[CH:22]2)[C:4]2[CH:5]=[CH:6][C:7]3[N:11]=[N:10][N:9]([CH3:12])[C:8]=3[CH:13]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 189243156-[bromo(4-chlorophenyl)methyl]-1-methyl-1H-benzotriazole monohydrobromide

Product 1

HCID 149908306-[(4-chlorophenyl)(1H-imidazol-1-yl)methyl]-1-methyl-1H-benzotriazoleYield 29.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 203 parts of 6-[bromo(4-chlorophenyl)methyl]-1-methyl-1H-benzotriazole monohydrobromide and 170 parts of 1H-imidazole in 1350 parts of methylbenzene was stirred for 28 hours at reflux temperature. The reaction mixture was allowed to cool to 80° C. and then evaporated. The oily residue was dissolved in dichloromethane. The organic layer was washed with a diluted hydrochloric acid solution. The separated aqueous layer was treated with a sodium hydroxide solution and extracted with dichloromethane. The combined dichloromethane layers were washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of dichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. To the residue were added 210 parts of 1,1'-oxybisethane and the whole was allowed to stand over weekend. The solid product was filtered off and dried at 50° C., yielding 48.1 parts (29.7%) of 6-[(4-chlorophenyl)(1H-imidazol-1 -yl)methyl]-1-methyl-1H-benzotriazole; mp. 87.7° C. (compound 63).

Workup

  1. temperatureat reflux temperature
  2. customevaporated
  3. dissolutionThe oily residue was dissolved in dichloromethane
  4. washThe organic layer was washed with a diluted hydrochloric acid solution
  5. additionThe separated aqueous layer was treated with a sodium hydroxide solution
  6. extractionextracted with dichloromethane
  7. washThe combined dichloromethane layers were washed with water
  8. customdried
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was purified by column chromatography over silica gel using
  12. additiona mixture of dichloromethane and methanol (95:5 by volume) as eluent
  13. customThe pure fractions were collected
  14. customthe eluent was evaporated
  15. additionTo the residue were added 210 parts of 1,1'-oxybisethane
  16. waitto stand over weekend
  17. filtrationThe solid product was filtered off
  18. customdried at 50° C.

Sources & evidence

ORD record
ord-867eca2fae494c71ac0e1eea2e7b9a30
Source dataset
uspto-grants-1990_07
Patent number
US04943574

Reaction notes

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