Sodium Carbonate → HCID 22265897, compound

HRID 489598Notes

Reaction equation

HRID 489598 reaction equation
[C:1]([NH:9][NH2:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.[C:16](=[O:19])([O-])[O-:17].[Na+].[Na+]>>[C:2]1([C:1]2[O:8][C:1]([C:2]3[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=3)[C:16]([OH:17])=[O:19])=[N:10][N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 11955BenzoylhydrazineHCID 24813Phosphorus oxychloride

Product 1

HCID 22265897HCID 22265897, compound

Conditions

Temperature
120 °C

Procedure

A mixture of methyl hydrogen isopthalalate (1.8 g, 10 mmol), benzoic hydrazide (1.4 g, 10 mmol) and phosphorous oxychloride (20 ml), under an atmosphere of nitrogen, was heated at 120° C. for 18 hours, then cooled to room temperature and then poured into ice water (500 ml). This mixture was treated with solid sodium carbonate until the aqueous layer was basic (pH 8-9) and the resultant pink solid was filtered. This material was treated with 100 ml methanol and the suspension was treated with sodium hydroxide solution (30 ml, 1M). The reaction mixture was heated at reflux for 4 hours, then cooled and then concentrated to dryness. The residue was dissolved in water (100 ml) and the solution was acidified to pH 3 by addition of concentrated hydrochloric acid. The resultant precipitate was filtered, then dried and then subjected to chromatography on silica gel eluting with a mixture of dichloromethane and methanol (98:2, v/v) to yield 3-(5-phenyl-1,3,4-oxadiazol-2-yl)-benzoic acid as a white solid (600 mg). 1H NMR [(CD3)2SO, 500 MHz]: δ 8.80 (s, 1H), 8.38 (m, 1H), 8.18 (m, 3H), 7.78 (m, 1H), 7.62 (m, 3H). MS(EI): 265(M+−H).

Workup

  1. temperaturecooled to room temperature
  2. filtrationthe resultant pink solid was filtered
  3. additionThis material was treated with 100 ml methanol
  4. additionthe suspension was treated with sodium hydroxide solution (30 ml, 1M)
  5. temperatureThe reaction mixture was heated
  6. temperatureat reflux for 4 hours
  7. temperaturecooled
  8. concentrationconcentrated to dryness
  9. dissolutionThe residue was dissolved in water (100 ml)
  10. additionthe solution was acidified to pH 3 by addition of concentrated hydrochloric acid
  11. filtrationThe resultant precipitate was filtered
  12. customdried
  13. additionsubjected to chromatography on silica gel eluting with a mixture of dichloromethane and methanol (98:2

Sources & evidence

ORD record
ord-968093e92d6c41db9474c16e2165cdf9
Source dataset
uspto-grants-2005_12
Patent number
US06977263B2

Reaction notes

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