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

HRID 223598

Reaction equation

HRID 223598 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 64092,2,2-TrifluoroethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4d2f82aacd4b40b9b3cb8c568cd4c23a
Source dataset
uspto-grants-1982_10
Patent number
US04355165

Linked notes

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