HCID 23544062, compound → HCID 21925587, compound

HRID 1243555Notes

Reaction equation

HRID 1243555 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][NH:6][C:7]([CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:11][CH2:10]1)=[O:8])=O>P(Cl)(Cl)(Cl)=O>[Cl:1][CH2:2][C:3]1[O:8][C:7]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[CH2:11][CH2:10]2)=[N:6][N:5]=1

Participants

3

Reactant 1

HCID 23544062HCID 23544062, compound

Product 1

HCID 21925587HCID 21925587, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

The hydrazide of Preparation 3 (20.4 g, 69 mmol) was suspended in phosphorus oxychloride (150 ml) at 100° C. for 4 hours. The mixture was cooled and the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate and was added to water. The aqueous layer was basified by addition of solid sodium hydrogen carbonate and the phases were separated. The aqueous phase was extracted with ethyl acetate (×2) and the combined organic layers were dried over magnesium sulphate and evaporated under reduced pressure. The material isolated was triturated with diethyl ether to give the title compound as a beige solid (15 g).

Workup

  1. temperatureThe mixture was cooled
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. additionwas added to water
  5. additionThe aqueous layer was basified by addition of solid sodium hydrogen carbonate
  6. customthe phases were separated
  7. extractionThe aqueous phase was extracted with ethyl acetate (×2)
  8. dry with materialthe combined organic layers were dried over magnesium sulphate
  9. customevaporated under reduced pressure
  10. customThe material isolated
  11. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-c13eaba31bf04f8fbad47e9d834f0ddf
Source dataset
uspto-grants-2006_10
Patent number
US07119088B2

Reaction notes

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