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

HRID 1732284노트

반응식

HRID 1732284 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-fa85351262914acaa05307cde6591482
출처 데이터셋
uspto-grants-1980_12
특허 번호
US04237132

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