Hydrochloric Acid → Flurtamone

HRID 978220Notes

Reaction equation

HRID 978220 reaction equation
Cl.[C:2]1([CH:8]2[C:12](=[O:13])[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=3)=[C:10]([NH2:24])[O:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25]N.CO>O>[C:2]1([CH:8]2[C:12](=[O:13])[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[CH:15]=3)=[C:10]([NH:24][CH3:25])[O:9]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 6329MethylamineHCID 13579285HCID 13579285, compound

Product 1

HCID 91755FlurtamoneYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In this example, 2.5 ml of aqueous 2N hydrochloric acid was added at room temperature to a stirred slurry containing 10 g of 2-phenyl-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran in 60 ml of aqueous 40 wt % methyl amine followed by the addition of 50 ml of methanol. The resulting suspension was heated to reflux and refluxed for about 24 hours and then allowed to cool and stand at room temperature for about 2 days. The mixture was then added to a dilute acid solution containing 58 ml of aqueous 12N hydrochloric acid in 300 ml of water and then extracted twice with methylene chloride. The methylene chloride extracts were combined and successively washed once with water, once with saturated aqueous sodium bicarbonate and once with saturated aqueous sodium chloride. The washed solution was dried over magnesium sulfate and evaporated under vacuum affording 9.7 g of the title compound as a pale yellow foam (yield=93%).

Workup

  1. customwas added at room temperature to a stirred slurry
  2. temperatureThe resulting suspension was heated
  3. temperatureto reflux
  4. temperaturerefluxed for about 24 hours
  5. temperatureto cool
  6. additionThe mixture was then added to a dilute acid solution
  7. extractionextracted twice with methylene chloride
  8. washsuccessively washed once with water, once with saturated aqueous sodium bicarbonate and once with saturated aqueous sodium chloride
  9. dry with materialThe washed solution was dried over magnesium sulfate
  10. customevaporated under vacuum

Sources & evidence

ORD record
ord-497f8012c93b4e62b49fe7d8bfb81a6b
Source dataset
uspto-grants-1987_05
Patent number
US04663466

Reaction notes

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