Dimethylformamide → 6-[(4-Chlorophenoxy)methyl]-4-phenylmorpholin-2-one

HRID 1732284Notes

Reaction equation

HRID 1732284 reaction equation
[NH:1]([CH2:8][CH:9]([OH:19])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:27][C:28](OCC)=[O:29].CN(C)C=O>O.C(OCC)(=O)C>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([O:11][CH2:10][CH:9]2[CH2:8][N:1]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:27][C:28](=[O:29])[O:19]2)=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 203059591-Anilino-3-(4-chlorophenoxy)propan-2-ol

Product 1

HCID 203059606-[(4-Chlorophenoxy)methyl]-4-phenylmorpholin-2-oneYield 56.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Two grams (0.0072 moles) of 1-anilino-3-(p-chlorophenoxy)-2-propanol [prepared in part (1)], 1.2 g (0.0087 moles) of K2CO3 and 2.9 g (0.0174 moles) of ethyl bromoacetate were added to 20 ml of N,N-dimethylformamide. The resulting mixture was refluxed for 5 hr with stirring. Concentration of the reaction mixture and addition of ethyl acetate and water to the residue gave a solid. The solid was collected by filtration and washed with ethyl acetate and water and dried (0.5 g). The filtrate was acidified with 10% aqueous hydrochloric acid and the organic layer was washed with water and dried over anhydrous magnesium sulfate. After the evaporation of ethyl acetate, 20 ml of acetic acid was added to the residue and refluxed for 3 hr. The reaction mixture was concentrated under reduced pressure, and 1.3 g of the solid was obtained by crystallizing the residue from ether. Recrystallization of the combined solids (1.8 g) from benzene gave 1.3 g (57%) of crystals, m.p.142°-144°.

Workup

  1. temperatureThe resulting mixture was refluxed for 5 hr
  2. customgave a solid
  3. filtrationThe solid was collected by filtration
  4. washwashed with ethyl acetate and water
  5. customdried (0.5 g)
  6. washthe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customAfter the evaporation of ethyl acetate, 20 ml of acetic acid
  9. additionwas added to the residue
  10. temperaturerefluxed for 3 hr
  11. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fa85351262914acaa05307cde6591482
Source dataset
uspto-grants-1980_12
Patent number
US04237132

Reaction notes

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