Phosphorus oxychloride → HCID 19875912, compound

HRID 1886371Notes

Reaction equation

HRID 1886371 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)[NH:14]3)=[CH:9][CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:13]1[C:12]([CH3:18])=[N:11][C:10]2[C:15]([N:14]=1)=[CH:16][C:7]([CH2:6][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)=[CH:8][CH:9]=2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 19875911HCID 19875911, compound

Product 1

HCID 19875912HCID 19875912, compoundYield 59.4%

Procedure

A mixture of 6 parts of 7-(1H-imidazol-1-ylmethyl)-3-methyl-2(1H)-quinoxalinone and 40 parts of phosphoryl chloride was stirred for 2 hours at reflux temperature. The reaction mixture was evaporated to dry. The residue was taken up in 300 parts of ice water and the whole was neutralized with potassium carbonate. The product 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 1,1'-oxybisethane. The product was filtered off and dried, yielding 1.6 parts (59.4%) of 3-chloro-6-(1H-imidazol-1-ylmethyl)-2-methylquinoxaline; mp. 115.8° C. (comp. 22).

Workup

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

Sources & evidence

ORD record
ord-3226d04ced5e48beae500d1c55a6f835
Source dataset
uspto-grants-1992_09
Patent number
US05151421

Reaction notes

Loading…