Hydrochloric Acid → Flurtamone

HRID 978219Notes

Reaction equation

HRID 978219 reaction equation
[Cl-].[CH3:2][NH3+].[C:4]1([CH:10]2[C:14](=[O:15])[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=3)=[C:12]([NH2:26])[O:11]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CN.Cl>O.CO>[C:4]1([CH:10]2[C:14](=[O:15])[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:23])([F:24])[F:25])[CH:17]=3)=[C:12]([NH:26][CH3:2])[O:11]2)[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 11637Methanamine, hydrochloride (1:1)HCID 13579285HCID 13579285, compound

Product 1

HCID 91755FlurtamoneYield 93.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In this example, 2 g of methylammonium chloride 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 overnight (about 15--18 hours). The mixture was cooled to room temperature and added to a dilute acid solution containing 58 ml of aqueous 12N hydrochloric acid in 300 ml of water. This mixture was 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 9.2 g of the title compound as a pale yellow foam (yield=88%).

Workup

  1. customwas added at room temperature to a stirred slurry
  2. temperatureThe resulting suspension was heated
  3. temperatureto reflux
  4. temperaturerefluxed overnight (about 15--18 hours)
  5. additionadded to a dilute acid solution
  6. extractionThis mixture was extracted twice with methylene chloride
  7. washsuccessively washed once with water, once with saturated aqueous sodium bicarbonate and once with saturated aqueous sodium chloride
  8. dry with materialThe washed solution was dried over magnesium sulfate
  9. customevaporated under vacuum

Sources & evidence

ORD record
ord-6c449a3662e54d6199d07159c091786c
Source dataset
uspto-grants-1987_05
Patent number
US04663466

Reaction notes

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