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

HRID 414165Notes

Reaction equation

HRID 414165 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:12](N)=[O:13])[C:5](=[CH:10][CH:11]=1)[C:6]([NH:8][CH3:9])=[O:7].[Cl:15][CH2:16][CH:17]1[O:19][CH2:18]1>FC(F)(F)CO>[Cl:15][CH2:16][CH:17]([OH:19])[CH2:18][NH:1][C:2]1[CH:3]=[C:4]2[C:12](=[O:13])[N:8]([CH3:9])[C:6](=[O:7])[C:5]2=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 7835EpichlorohydrinHCID 212817404-amino-N-methylphthalamide

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 (0.142 mole) 4-amino-N-methylphthalamide, prepared according to the method described in J. Chem. Soc. 26: (1937), 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 hrs. 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 intermediate m.p. 136°-138.5° C. Calculated for C12H13ClN2O3 ; C, 53.64; H, 4.88; N, 10.45. Found: C, 53.87; H, 4.85; N, 10.81.

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-5e16197f52484eb7aae16d085b371eac
Source dataset
uspto-grants-1988_12
Patent number
US04791055

Reaction notes

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