Water → Flurtamone

HRID 978218Notes

Reaction equation

HRID 978218 reaction equation
[C:1]1([CH:7]2[C:11](=[O:12])[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=3)=[C:9]([NH2:23])[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN.O1C=CC[CH2:27]1.O>CO>[C:1]1([CH:7]2[C:11](=[O:12])[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:20])([F:21])[F:22])[CH:14]=3)=[C:9]([NH:23][CH3:27])[O:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6329Methylamine2×HCID 709342,3-DihydrofuranHCID 13579285HCID 13579285, compound

Product 1

HCID 91755Flurtamone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In this example, a mixture containing 0.5 g of 2-phenyl-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran ("dihydrofuran starting material") and 25 ml of aqueous 40 wt. % methylamine in 10 ml of methanol was refluxed for 18 hours. The mixture was analyzed by thin-layer chromatography for the dihydrofuran starting material. Another 10 ml of aqueous 40 wt. % methylamine was added and the mixture refluxed for about four hours. The mixture was cooled, poured into 100 ml of water and extracted several times with ethyl ether. The organic extracts were dried over magnesium sulfate, concentrated in vacuo and chromatographed using 3% tetrahydrofuran/chloroform as eluent to yield 0.36 g of the title compound.

Workup

  1. temperaturewas refluxed for 18 hours
  2. temperaturethe mixture refluxed for about four hours
  3. temperatureThe mixture was cooled
  4. extractionextracted several times with ethyl ether
  5. dry with materialThe organic extracts were dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customchromatographed

Sources & evidence

ORD record
ord-c5981bcf5df14affab1d8752a72f6972
Source dataset
uspto-grants-1987_05
Patent number
US04663466

Reaction notes

Loading…