Water → HCID 59598347, compound

HRID 2359665Notes

Reaction equation

HRID 2359665 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][N:7]1[C:11]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[CH:10][C:9](=[O:18])[N:8]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[Na+].O.CN([CH:31]=[O:32])C>>[CH3:6][N:7]1[C:11]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[C:10]([CH:31]=[O:32])[C:9](=[O:18])[N:8]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 59598355HCID 59598355, compound

Product 1

HCID 59598347HCID 59598347, compound

Procedure

To a 25 ml round-bottom flask with stirbar was added N,N-dimethylformamide (10.0 ml, 130 mmol). The flask was cooled in an ice water bath, and phosphorous oxychloride (4.2 ml, 45 mmol) was added. The reaction was warmed to room temperature and stirred under nitrogen. After 50 minutes, this was transferred, first via syringe and then pipette, to a solution of 1-methyl-2-phenyl-5-(pyridin-4-yl)-1,2-dihydropyrazol-3-one (3.31 g, 13 mmol) in DMF (18 ml). The flask was placed in a preheated oil bath (120 C), stirred for 12 minutes, and then cooled to room temperature. The reaction was poured into a aqueous solution of 5 N NaOH (40 ml) and diluted with ice water (˜75 ml). More ice and water were added. The aqueous phase was extracted with chloroform and the organic extracts were dried over sodium sulfate, filtered, and concentrated. DMF present, so the crude material was diluted with chloroform and washed with water. The aqueous extractions were extracted with chloroform, and the organic layers were combined, dried over sodium sulfate, filtered, and concentrated to give the crude product. MS (ESI pos. ion) m/z: 280 (MH+). Calc'd exact mass for C16H13N3O2: 279. Material taken to next step without further purification.

Workup

  1. temperatureThe flask was cooled in an ice water bath
  2. customthis was transferred, first via syringe
  3. customThe flask was placed in a preheated oil bath
  4. stirring(120 C), stirred for 12 minutes
  5. temperaturecooled to room temperature
  6. extractionThe aqueous phase was extracted with chloroform
  7. dry with materialthe organic extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. additionDMF present, so the crude material was diluted with chloroform
  11. washwashed with water
  12. extractionThe aqueous extractions
  13. extractionwere extracted with chloroform
  14. dry with materialdried over sodium sulfate
  15. filtrationfiltered
  16. concentrationconcentrated

Sources & evidence

ORD record
ord-0ef84b91dfca41458f372b80cb4e6ae0
Source dataset
uspto-grants-2014_04
Patent number
US08685983B2

Reaction notes

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