Methyl iodide → HCID 14990628, compound

HRID 2166046Notes

Reaction equation

HRID 2166046 reaction equation
[C:1]1([CH:7]([C:9]2[CH:17]=[CH:16][C:12]3[NH:13][N:14]=[N:15][C:11]=3[CH:10]=2)[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[H][H].I[CH3:23]>CN(C)C=O>[CH3:23][N:15]1[C:11]2[CH:10]=[C:9]([CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[OH:8])[CH:17]=[CH:16][C:12]=2[N:13]=[N:14]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178418361HCID 178418361, compoundHCID 178519465HCID 178519465, compound

Product 1

HCID 14990628HCID 14990628, compoundYield 12.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 22.5 parts of α-phenyl-1H-benzotriazole-5-methanol, 4.8 parts of a sodium hydride dispersion 50% and 90 parts of N,N-dimethylformamide was stirred till hydrogen production had ceased. After the addition of 14.2 parts of iodomethane, stirring was continued for 30 minutes at room temperature. The mixture was concentrated. The concentrate was taken up in 50 parts of water and the product was extracted with dichloromethane. The extract was dried, filtered and concentrated. The concentrate was purified by filtration over silica gel using a mixture of trichloromethane and methanol (99:1 by volume) as eluent. The desired fraction was collected and the eluent was evaporated. The two isomers were separated by crystallization from ethyl acetate. The first isomer was further purified by crystallisation from ethyl acetate. The product was filtered off and dried, yielding 3 parts (12.5%) of 1-methyl-α-phenyl-1H-benzotriazole-6-methanol; mp. 145° C. (int. 71).

Workup

  1. concentrationThe mixture was concentrated
  2. extractionthe product was extracted with dichloromethane
  3. customThe extract was dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. filtrationThe concentrate was purified by filtration over silica gel using
  7. additiona mixture of trichloromethane and methanol (99:1 by volume) as eluent
  8. customThe desired fraction was collected
  9. customthe eluent was evaporated
  10. customThe two isomers were separated by crystallization from ethyl acetate
  11. customThe first isomer was further purified by crystallisation from ethyl acetate
  12. filtrationThe product was filtered off
  13. customdried

Sources & evidence

ORD record
ord-c466023678e54f50b4e4fdebe8d59285
Source dataset
uspto-grants-1990_07
Patent number
US04943574

Reaction notes

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