((o-Methoxyphenoxy)methyl)oxirane → HCID 12608619, compound

HRID 1278357Notes

Reaction equation

HRID 1278357 reaction equation
[O:1]1[CH2:13][CH:2]1[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12].[F:14][C:15]1[CH:32]=[CH:31][C:18]([C:19]([NH:21][C:22]([NH:24][CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[O:23])=[O:20])=[CH:17][CH:16]=1>C(O)(C)C>[F:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([NH:21][C:22](=[O:23])[NH:24][CH:25]2[CH2:26][CH2:27][N:28]([CH2:13][CH:2]([OH:1])[CH2:3][O:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[O:11][CH3:12])[CH2:29][CH2:30]2)=[O:20])=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 98357((o-Methoxyphenoxy)methyl)oxiraneHCID 12608597HCID 12608597, compound

Product 1

HCID 12608619HCID 12608619, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-(2,3-Epoxypropoxy)anisole (0.99 g, 0.0055 m) and 1-(4-fluorobenzoyl)-3-(piperid-4-yl)urea (1.32 g, 0.005 m) in isopropyl alcohol (50 cm3) were refluxed for 24 hours. The solution was cooled and the product which crystallised was filtered off. This was dissolved in ethanol and acidified with ethanolic hydrogen chloride. The solution was heated on a water bath and ethyl acetate was added to replace the lost solvent. The product crystallised out and was recrystallised twice from ethanol giving the title compound as the hydrochloride, hemihydrate (0.44 g) m.p. 194°-195° C.

Workup

  1. temperatureThe solution was cooled
  2. customthe product which crystallised
  3. filtrationwas filtered off
  4. dissolutionThis was dissolved in ethanol
  5. temperatureThe solution was heated on a water bath
  6. additionethyl acetate was added
  7. customThe product crystallised out
  8. customwas recrystallised twice from ethanol giving the title compound as the hydrochloride, hemihydrate (0.44 g) m.p. 194°-195° C.

Sources & evidence

ORD record
ord-32f46e491cff48da8a363d035f08e9c4
Source dataset
uspto-grants-1981_07
Patent number
US04281132

Reaction notes

Loading…