Potassium Carbonate → HCID 14990943, compound

HRID 2248342Notes

Reaction equation

HRID 2248342 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.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[CH:26]=1>CN(C)C=O>[N:1]1([CH2:6][C:7]2[CH:8]=[CH:9][C:10]3[N:14]=[N:13][N:12]([O:15][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[CH:26]=4)[C:11]=3[CH:16]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12102m-Xylyl chlorideHCID 14990941HCID 14990941, compound

Product 1

HCID 14990943HCID 14990943, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.2 parts of 6-(1H-imidazol-1-ylmethyl)-1H-benzotriazol-1-ol, 1 part of potassium carbonate and 27 parts of N,N-dimethylformamide was stirred for 30 minutes at room temperature. 2.1 Parts of 1-(chloromethyl)-3-methylbenzene were added and stirring was continued for 3 hours at room temperature. The mixture was allowed to stand overnight at room temperature and was evaporated. The residue was diluted with water and the product was extracted with dichloromethane. The extract was dried, filtered and concentrated. The concentrate 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 solid residue was crystallized from a mixture of ethyl acetate and 2,2'-oxybispropane (10:20 by volume). The product was filtered off, washed with 2,2'-oxybispropane and dried, yielding 3.4 parts (70.9%) of 6-(1H-imidazol-1-ylmethyl)-1-[(3-methylphenyl)methoxy]-1H-benzotriazole; mp. 120.1° C. (compound 160). In a similar manner there were also prepared:

Workup

  1. stirringstirring
  2. waitwas continued for 3 hours at room temperature
  3. waitto stand overnight at room temperature
  4. customwas evaporated
  5. additionThe residue was diluted with water
  6. extractionthe product was extracted with dichloromethane
  7. customThe extract was dried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe concentrate was purified by column chromatography over silica gel using
  11. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  12. customThe pure fractions were collected
  13. customthe eluent was evaporated
  14. customThe solid residue was crystallized from a mixture of ethyl acetate and 2,2'-oxybispropane (10:20 by volume)
  15. filtrationThe product was filtered off
  16. washwashed with 2,2'-oxybispropane
  17. customdried

Sources & evidence

ORD record
ord-f65073e405aa4eb8addd9b0473505493
Source dataset
uspto-grants-1991_08
Patent number
US05039677

Reaction notes

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