Phosphorus oxychloride → 2-Chloro-5-(3-methoxyphenyl)benzimidazole

HRID 496265Notes

Reaction equation

HRID 496265 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:18]=[CH:17][C:12]3[NH:13][C:14](=O)[NH:15][C:11]=3[CH:10]=2)[CH:6]=[CH:7][CH:8]=1.P(Cl)(Cl)([Cl:21])=O>[Cl-].C[N+](C)(C)C>[Cl:21][C:14]1[NH:15][C:11]2[CH:10]=[C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:18]=[CH:17][C:12]=2[N:13]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 223253275-(3-Methoxyphenyl)benzimidazolidin-2-one

Product 1

HCID 120716652-Chloro-5-(3-methoxyphenyl)benzimidazole

Reagents, catalysts & solvents 1

HCID 6379Tetramethylammonium chlorideCatalyst

Procedure

Heat a mixture of 5-(3-methoxyphenyl)benzimidazolidin-2-one (1.4 g) and tetramethylammonium chloride (ca. 2 g) in phosphorous oxychloride at 100° C. for 8 hours. After cooling, concentrate the mixture in vacuo, triturate with water, and neutralize with ammonium hydroxide. Collect the precipitate and air-dry to obtain 2-chloro-5-(3-methoxyphenyl)benzimidazole. D. 1′-(5-(3-methoxyphenyl)-1H-benzimidazol-2-yl)-spiro[isobenzofuran-1,4′-piperidin]-3-one

Workup

  1. temperatureHeat
  2. temperatureAfter cooling
  3. concentrationconcentrate the mixture in vacuo
  4. customtriturate with water
  5. customCollect the precipitate
  6. customair-dry

Sources & evidence

ORD record
ord-1e5fed3f8109450d96327e05bdb3b0d1
Source dataset
uspto-grants-2005_09
Patent number
US06943199B2

Reaction notes

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