1-Propanol → HCID 19875913, compound

HRID 1886372Notes

Reaction equation

HRID 1886372 reaction equation
[Na].Cl[C:3]1[C:4]([CH3:19])=[N:5][C:6]2[C:11]([N:12]=1)=[CH:10][C:9]([CH2:13][N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1)=[CH:8][CH:7]=2.[CH2:20]([OH:23])[CH2:21][CH3:22]>>[N:14]1([CH2:13][C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=2)[N:5]=[C:4]([CH3:19])[C:3]([O:23][CH2:20][CH2:21][CH3:22])=[N:12]3)[CH:18]=[CH:17][N:16]=[CH:15]1

Participants

4

Reactant 3

HCID 10311-PropanolHCID 5360545SodiumHCID 19875912HCID 19875912, compound

Product 1

HCID 19875913HCID 19875913, compoundYield 57.1%

Procedure

A solution of 0.3 parts of sodium in 24 parts of 1-propanol was added to 2.4 parts of 3-chloro-6-(1H-imidazol-1-ylmethyl)-2-methylquinoxaline. The whole was stirred for 2 hours at reflux temperature. The reaction mixture was evaporated and the residue was extracted three times with 65 parts of dichloromethane. The combined extracts were 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 pentane and 2,2'-oxybispropane. The product was filtered off and dried, yielding 1.5 parts (57.1%) of 6-(1H-imidazol-1-ylmethyl)-2-methyl-3-propoxyquinoxaline; mp. 85.5° C. (comp. 24).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. extractionthe residue was extracted three times with 65 parts of dichloromethane
  4. customThe combined extracts were dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of dichloromethane and methanol (98:2 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. customThe residue was crystallized from a mixture of pentane and 2,2'-oxybispropane
  12. filtrationThe product was filtered off
  13. customdried

Sources & evidence

ORD record
ord-766037fb7df24300a92e982c65369aba
Source dataset
uspto-grants-1992_09
Patent number
US05151421

Reaction notes

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