Phosphorus oxychloride → HCID 19875912, compound
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]=2Participants
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
- temperatureat reflux temperature
- customThe reaction mixture was evaporated
- customto dry
- extractionThe product was extracted three times with 65 parts of dichloromethane
- customThe combined extracts were dried
- filtrationfiltered
- customevaporated
- customThe residue was purified by column chromatography over silica gel using
- additiona mixture of dichloromethane and methanol (98:2 by volume) as eluent
- customThe pure fractions were collected
- customthe eluent was evaporated
- customThe residue was crystallized from 1,1'-oxybisethane
- filtrationThe product was filtered off
- customdried
Sources & evidence
- ORD record
- ord-7ecca9f8ae7e40dab350f3a814a8dc45
- Source dataset
- uspto-grants-1991_07
- Patent number
- US05028606
Reaction notes
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