Phosphorus oxide (P4O10) → 5,6-Dichloro-2-(4-cyano-2-methoxyphenyl)benzimidazole

HRID 1352653Notes

Reaction equation

HRID 1352653 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[CH:4][C:3]=1[NH:10][C:11](=O)[C:12]1[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][C:13]=1[O:20][CH3:21].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C1(C)C(C)=CC=CC=1>[Cl:9][C:5]1[C:6]([Cl:8])=[CH:7][C:2]2[N:1]=[C:11]([C:12]3[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][C:13]=3[O:20][CH3:21])[NH:10][C:3]=2[CH:4]=1

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)2×HCID 21101177N-(2-amino-4,5-dichlorophenyl)-2-methoxy-4-cyanobenzamide

Product 1

HCID 211011705,6-Dichloro-2-(4-cyano-2-methoxyphenyl)benzimidazoleYield 73.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A suspension of N-(2-amino-4,5-dichlorophenyl)-2-methoxy-4-cyanobenzamide (2.9 g, 8.6 mmol) and P2O5 (2.9 g, 10 mmol) in xylene (48 ml) was refluxed for 24 h. Additional P2O5 (2.9 g, 10 mmol) was added and the mixture was refluxed for 42 h. Solvent was removed under reduced pressure. The residue was treated with 2N NaOH (50 ml) and extracted with ethyl acetate (100 ml). The organic layer was washed with water and brine, dried over Na2SO4, filtered and evaporated under reduced pressure to give 2 g of the title compound (yield 73%), mp>250° C.

Workup

  1. temperaturewas refluxed for 24 h
  2. temperaturethe mixture was refluxed for 42 h
  3. customSolvent was removed under reduced pressure
  4. additionThe residue was treated with 2N NaOH (50 ml)
  5. extractionextracted with ethyl acetate (100 ml)
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f4130c369ea64616af7cce3dfbbb51ba
Source dataset
uspto-grants-2007_05
Patent number
US07220769B2

Reaction notes

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