Epichlorohydrin → 4-(3-chloro-2-hydroxypropylamino)-N-methylphthalimide

HRID 443741

반응식

HRID 443741 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[N:8]([CH3:11])[C:6](=[O:7])[C:5]2=[CH:12][CH:13]=1.[Cl:14][CH2:15][CH:16]1[O:18][CH2:17]1>FC(F)(F)CO>[Cl:14][CH2:15][CH:16]([OH:18])[CH2:17][NH:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[N:8]([CH3:11])[C:6](=[O:7])[C:5]2=[CH:12][CH:13]=1

참가 물질

4

반응물 2

HCID 7835EpichlorohydrinHCID 7269315-amino-2-methyl-2,3-dihydro-1H-isoindole-1,3-dione

생성물 1

HCID 212817364-(3-chloro-2-hydroxypropylamino)-N-methylphthalimide수율 77.3%

시약·촉매·용매 1

HCID 64092,2,2-Trifluoroethanol용매

실험 절차

Twenty-five grams (g) (0.142 mole) 4-amino-N-methylphthalimide [Flitsch, Chem. Ber. 94:2494(1961)] and 20.7 g (0.21 mole) 1-chloro-2,3-epoxypropane were added to 150 ml 2,2,2-trifluoroethanol and the reaction mixture was heated to reflux with stirring for 48 hours. Seventy to eighty ml of 2,2,2-trifluoroethanol was removed by distillation and a heavy yellow precipitate formed when the remaining solution cooled to room temperature. This precipitate was triturated with ethyl acetate, collected by filtration and dried to give 29.5 g (77% yield) of the desired phthalimide intermediate m.p. 136°-138.5° C.

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux
  3. customSeventy to eighty ml of 2,2,2-trifluoroethanol was removed by distillation
  4. customa heavy yellow precipitate formed when the remaining solution
  5. customThis precipitate was triturated with ethyl acetate
  6. filtrationcollected by filtration
  7. customdried

출처 및 근거

ORD 기록
ord-7b0f148de66d487c812caba10f9fd673
출처 데이터셋
uspto-grants-1981_04
특허 번호
US04261893

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