Isopropyl iodide → HCID 14990987, compound

HRID 2166064Notes

Reaction equation

HRID 2166064 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+].I[CH:24]([CH3:26])[CH3:25]>CS(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][CH:24]([CH3:26])[CH3:25])[C:11]=3[CH:16]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 14990941HCID 14990941, compound

Product 1

HCID 14990987HCID 14990987, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 3.23 parts of 6-(1H-imidazol-1-ylmethyl)-1H-benzotriazol-1-ol, 2.07 parts of potassium carbonate and 20 parts of dimethyl sulfoxide was stirred for 10 minutes at room temperature. Then there were added 2.55 parts of 2-iodopropane and stirring was continued first for 15 minutes at room temperature and then for 1 hour at 50° C. The reaction mixture was evaporated. 50 Parts of water were added. The product was extracted with dichloromethane. The extract was dried, filtered and 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 crystallized from 14 parts of 1,1'-oxybisethane. The product was filtered off and dried, yielding 3.3 parts (85.5%) of 6-(1H-imidazol-1-ylmethyl)-1-(1-methylethoxy)-1H-benzotriazole; mp. 114.3° C. (compound 195).

Workup

  1. stirringstirring
  2. waitwas continued first for 15 minutes at room temperature
  3. waitfor 1 hour at 50° C
  4. customThe reaction mixture was evaporated
  5. addition50 Parts of water were added
  6. extractionThe product was extracted with dichloromethane
  7. customThe extract was dried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue 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 residue was crystallized from 14 parts of 1,1'-oxybisethane
  15. filtrationThe product was filtered off
  16. customdried

Sources & evidence

ORD record
ord-85d5f499c5964618a8e87a789ad1dabd
Source dataset
uspto-grants-1990_07
Patent number
US04943574

Reaction notes

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