Phosphorus oxychloride → Methyl 2-chloro-1-[(2'-cyanobiphenyl-4-yl)methyl]benzimidazole-7-carboxylate

HRID 612769Notes

Reaction equation

HRID 612769 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]3[C:21]([C:25]([O:27][CH3:28])=[O:26])=[CH:22][CH:23]=[CH:24][C:19]=3[NH:18][C:17]2=O)=[CH:11][CH:10]=1)#[N:2].P(Cl)(Cl)([Cl:32])=O>>[Cl:32][C:17]1[N:16]([CH2:15][C:12]2[CH:13]=[CH:14][C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:1]#[N:2])=[CH:10][CH:11]=2)[C:20]2[C:21]([C:25]([O:27][CH3:28])=[O:26])=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 15654691Methyl 3-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-4-carboxylate

Product 1

HCID 15654692Methyl 2-chloro-1-[(2'-cyanobiphenyl-4-yl)methyl]benzimidazole-7-carboxylateYield 28%

Procedure

A mixture of methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-oxo-2,3-dihydrobenzimidazole-7-carboxylate (8.02 g) in phosphorus oxychloride (30 ml) was heated under reflux for 8 hours. The reaction mixture was concentrated and the resulting residue was poured into ice-water. The mixture was extracted with chloroform. The extract was washed with water, dried and evaporated. The residue was purified by column chromatography on silica gel to give crystals, which were recrystallized from chloroform--methanol to afford colorless needles (2.2 g, 28%), m.p. 154-157° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 8 hours
  3. concentrationThe reaction mixture was concentrated
  4. additionthe resulting residue was poured into ice-water
  5. extractionThe mixture was extracted with chloroform
  6. washThe extract was washed with water
  7. customdried
  8. customevaporated
  9. customThe residue was purified by column chromatography on silica gel
  10. customto give crystals, which
  11. customwere recrystallized from chloroform

Sources & evidence

ORD record
ord-3caf4fabdf2b45fda3185da4f6670446
Source dataset
uspto-grants-1999_12
Patent number
US06004989

Reaction notes

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