Epichlorohydrin → 4-Chloro-4'-[(2,3-epoxypropyl)amino]benzophenone

HRID 653114Notes

Reaction equation

HRID 653114 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[CH2:17]([CH:19]1[O:21][CH2:20]1)Cl.C(=O)([O-])[O-].[K+].[K+]>>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][CH2:17][CH:19]3[O:21][CH2:20]3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 35287064-Amino-4'-chlorobenzophenone

Product 1

HCID 201865924-Chloro-4'-[(2,3-epoxypropyl)amino]benzophenone

Procedure

23.2 g of 4-chloro-4'-aminobenzophenone, 92 g of epichlorohydrin and 7 g of potassium carbonate were heated at reflux for 15 hours. The excess epichlorohydrin was evaporated in vacuo and the solid residue was partitioned between water and chloroform. From the organic phase there was obtained 4-chloro-4'-[(2,3-epoxypropyl)amino]benzophenone which was recrystallized twice from methanol, m.p. 128°-129° C.

Workup

  1. temperatureat reflux for 15 hours
  2. customThe excess epichlorohydrin was evaporated in vacuo
  3. customthe solid residue was partitioned between water and chloroform

Sources & evidence

ORD record
ord-bb31ad61fbdb454f81bfb79e92d6882c
Source dataset
uspto-grants-1987_06
Patent number
US04675328

Reaction notes

Loading…