Ethyl Acetate → N-{2-[(benzyloxy)amino]ethyl}phthalimide

HRID 223654Notes

Reaction equation

HRID 223654 reaction equation
BrCC[C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:7]([NH:9][C:10](=[O:11])[C:5]=12)=[O:8].[CH2:15]([O:22][NH2:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:24](OCC)(=O)[CH3:25]>>[CH2:15]([O:22][NH:23][CH2:24][CH2:25][N:9]1[C:10](=[O:11])[C:5]2=[CH:4][CH:14]=[CH:13][CH:12]=[C:6]2[C:7]1=[O:8])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 102313O-BenzylhydroxylamineHCID 219600212-Bromoethylphthalimide

Product 1

HCID 18787878N-{2-[(benzyloxy)amino]ethyl}phthalimide

Procedure

A mixture of 12.30 g. of 2-bromoethyl-phthalimide and 12.31 g. of O-benzylhydroxylamine is warmed to 80° for 48 hours. Ethyl acetate is then added, and the precipitate formed is filtered off with suction. The mother liquor is evaporated in vacuo. 35 ml. of methanol are added to the oily residue and the mixture is left to stand at room temperature overnight. The crystalline precipitate is filtered off with suction and dried. The resulting crude product melts at 90°-91°. Analytically pure N-{2-[(benzyloxy)amino]ethyl}phthalimide, m.p. 92°-94°, is obtained by recrystallization from methanol.

Workup

  1. additionA mixture of 12.30 g
  2. customthe precipitate formed
  3. filtrationis filtered off with suction
  4. customThe mother liquor is evaporated in vacuo
  5. additionof methanol are added to the oily residue
  6. waitthe mixture is left
  7. filtrationThe crystalline precipitate is filtered off with suction
  8. customdried

Sources & evidence

ORD record
ord-99e0d43da7f548f3b560f668fe9840b8
Source dataset
uspto-grants-1982_10
Patent number
US04355033

Reaction notes

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