Water → 3-(2-(4-Chlorophenoxy)phenyl)-1-methylpyrrolidine-2,4-dione

HRID 1625163노트

반응식

HRID 1625163 반응식
CC(C)([O-])C.[K+].C([O:9][C:10](=O)[CH2:11][N:12]([C:14](=[O:30])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)[CH3:13])C.O>C1(C)C=CC=CC=1>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([O:22][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH:15]2[C:10](=[O:9])[CH2:11][N:12]([CH3:13])[C:14]2=[O:30])=[CH:24][CH:25]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 68001731ethyl 2-(2-(2-(4-chlorophenoxy)phenyl)-N-methylacetamido)acetate

생성물 1

HCID 231486583-(2-(4-Chlorophenoxy)phenyl)-1-methylpyrrolidine-2,4-dione

시약·촉매·용매 1

HCID 1140Toluene용매2회

반응 조건

온도
27.5 °C

실험 절차

To a suspension of potassium tert-butoxide (88 g) in toluene (1000 mL) is added a solution of ethyl-N-[2-[2-(4-chlorophenoxy)phenyl]acetyl]-N-methylglycinate (250 g) in toluene (1000 mL), under nitrogen at 15-25° C. and the mixture is maintained for 12-15 hours at 25-30° C. Water (3000 mL) is added and the mass is maintained for 1-2 hours at 0-5° C. Organic and aqueous layers are separated and the organic layer is washed with water (1000 mL). Aqueous layers are combined and washed with ethyl acetate (2000 mL). The pH of combined aqueous layers is adjusted to 2-2.5 by addition of aqueous HCl (100 mL) at 0-5° C. The solid is collected by filtration and washed with water (200 mL), then is dried to afford the crude title compound. The crude compound is further purified by heating at reflux a solution of crude 3-(2-(4-chlorophenoxy)phenyl)-1-methylpyrrolidine-2,4-dione in toluene (3600 mL) for 30-60 minutes, followed by cooling to room temperature. Solid that forms is collected by filtration, washed with hexane (500 mL), and dried to afford a purified title compound. Yield: 130 g. Purity by HPLC: 99.48%.

후처리

  1. temperaturethe mass is maintained for 1-2 hours at 0-5° C
  2. customOrganic and aqueous layers are separated
  3. washthe organic layer is washed with water (1000 mL)
  4. washwashed with ethyl acetate (2000 mL)
  5. additionThe pH of combined aqueous layers is adjusted to 2-2.5 by addition of aqueous HCl (100 mL) at 0-5° C
  6. filtrationThe solid is collected by filtration
  7. washwashed with water (200 mL)
  8. customis dried

출처 및 근거

ORD 기록
ord-4895338e0081486ba8bae0e1b963f07f
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08779161B2

반응 노트

불러오는 중…