Phosphorus oxychloride → HCID 178497361, compound

HRID 538179Notes

Reaction equation

HRID 538179 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:8]2[NH:9][C:10](=O)[NH:11][C:7]=2[CH:6]=1)=[O:4].P(Cl)(Cl)([Cl:17])=O>>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:8]2[NH:9][C:10]([Cl:17])=[N:11][C:7]=2[CH:6]=1)=[O:4]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 10352553methyl 2-oxo-2,3-dihydro-1H-1,3-benzodiazole-5-carboxylate

Product 1

HCID 178497361HCID 178497361, compoundYield 95%

Conditions

Temperature
100 °C

Procedure

2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid methyl ester (3.00 g, 15.6 mmol) and phosphorus oxychloride (30 mL) were combined and heated to 100° C. for 48 h. The mixture was cooled to 23° C. and concentrated under reduced pressure. The residue was cooled to 0° C., and cold, saturated aqueous NaHCO3 (60 mL) was added cautiously. After stirring at 23° C. for 15 min, the mixture was sonicated and the resulting residue was filtered to yield the titled compound (3.13 g, 95%), which was used in the next step without further purification. MS (ESI/CI): mass calcd. for C9H7ClN2O2, 210.02; m/z found, 211.0 [M+H]+.

Workup

  1. temperatureThe mixture was cooled to 23° C.
  2. concentrationconcentrated under reduced pressure
  3. temperatureThe residue was cooled to 0° C.
  4. additioncold, saturated aqueous NaHCO3 (60 mL) was added cautiously
  5. customthe mixture was sonicated
  6. filtrationthe resulting residue was filtered

Sources & evidence

ORD record
ord-c33cdf0f7e164b4ba4c9295b8b683c13
Source dataset
uspto-grants-2014_10
Patent number
US08865713B2

Reaction notes

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