HCID 14990687, compound → HCID 14990688, compound

HRID 2248330Notes

Reaction equation

HRID 2248330 reaction equation
Br[CH:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1.[CH3:19][C:20]1[N:21]=[CH:22][NH:23][CH:24]=1>C(#N)C>[Cl:9][C:6]1[CH:7]=[CH:8][C:3]([CH:2]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:23]2[CH:24]=[C:20]([CH3:19])[N:21]=[CH:22]2)=[CH:4][C:5]=1[N+:10]([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 14990687HCID 14990687, compoundHCID 178418800HCID 178418800, compound

Product 1

HCID 14990688HCID 14990688, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 31.9 parts of 4-(bromophenylmethyl)-1-chloro-2-nitrobenzene, 49.3 parts of 4-methyl-1H-imidazole and 120 parts of acetonitrile was stirred for 24 hours at reflux temperature. The reaction mixture was concentrated and the concentrate was taken up in 150 parts of water. 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 trichloromethane, methanol and methanol, saturated with ammonia, (98:1:1 by volume) as eluent. The desired fractions were collected and the eluent was evaporated. The residue was converted into the ethanedioate salt in 80 parts of 2-propanol. The salt was filtered off, washed with 2-propanol and dried, yielding 22.8 parts (54.5%) of 1-[(4-chloro-3-nitrophenyl)phenylmethyl]-4-methyl-1H-imidazole ethanediotate(1:1); mp. 105° C. (int. 133).

Workup

  1. temperatureat reflux temperature
  2. concentrationThe reaction mixture was concentrated
  3. extractionThe product was extracted with dichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane, methanol and methanol
  9. customThe desired fractions were collected
  10. customthe eluent was evaporated
  11. filtrationThe salt was filtered off
  12. washwashed with 2-propanol
  13. customdried

Sources & evidence

ORD record
ord-4ca1f78634fd4ac6b945fc5cdc070f1f
Source dataset
uspto-grants-1991_08
Patent number
US05039677

Reaction notes

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