Methyl iodide → HCID 67791407, compound

HRID 1086221Notes

Reaction equation

HRID 1086221 reaction equation
[N:1]1([CH2:6][C:7]2[CH:16]=[C:15]3[C:10]([N:11]=[C:12]([CH3:18])[C:13](=[O:17])[NH:14]3)=[CH:9][CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[OH-].[Na+].I[CH3:22]>CN(C)C=O>[OH2:17].[N:1]1([CH2:6][C:7]2[CH:16]=[C:15]3[C:10]([N:11]=[C:12]([CH3:18])[C:13](=[O:17])[N:14]3[CH3:22])=[CH:9][CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[N:1]1([CH2:6][C:7]2[CH:16]=[C:15]3[C:10]([N:11]=[C:12]([CH3:18])[C:13](=[O:17])[N:14]3[CH3:22])=[CH:9][CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 19875911HCID 19875911, compound

Product 1

HCID 67791407HCID 67791407, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3 parts of 7-(1H-imidazol-1-ylmethyl)-3-methyl-2(1H)-quinoxalinone, 0.3 parts of a sodium hydroxide dispersion 50% and 28 parts of N,N-dimethylformamide was stirred for 1.5 hours at room temperature. 2 Parts of iodomethane were added and stirring was continued for 12 hours at room temperature under nitrogen atmosphere. The reaction mixture was evaporated to dry and the residue was taken up in water and potassium carbonate. 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 dichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 2,2'-oxybispropane and 2-propanone. The product was filtered off and dried, yielding 2.2 parts (66.8%) of 7-(1H-imidazol-1-ylmethyl)-1,3-dimethyl-2(1H)-quinoxalinone hemihydrate; mp. 128.6° C. (comp. 79).

Workup

  1. stirringstirring
  2. waitwas continued for 12 hours at room temperature under nitrogen atmosphere
  3. customThe reaction mixture was evaporated
  4. customto dry
  5. extractionThe product was extracted with dichloromethane
  6. customThe extract was dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography over silica gel using
  10. additiona mixture of dichloromethane and methanol (98:2 by volume) as eluent
  11. customThe pure fractions were collected
  12. customthe eluent was evaporated
  13. customThe residue was crystallized from a mixture of 2,2'-oxybispropane and 2-propanone
  14. filtrationThe product was filtered off
  15. customdried

Sources & evidence

ORD record
ord-ed4ab71481a741ee9692f6bb3b1492c1
Source dataset
uspto-grants-1991_07
Patent number
US05028606

Reaction notes

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