Dimethyl Sulfoxide → N-[alpha-(t-butoxycarbonyl) benzyloxy] phthalimide

HRID 614444Notes

Reaction equation

HRID 614444 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].C(=O)([O-])[O-].[K+].[K+].Br[CH:20]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].CS(C)=O>O>[C:24]([O:23][C:21]([CH:20]([O:1][N:2]1[C:3](=[O:12])[C:4]2=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]2[C:6]1=[O:7])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:22])([CH3:27])([CH3:25])[CH3:26]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10665N-HydroxyphthalimideHCID 11430Potassium CarbonateHCID 11000147Tert-butyl 2-bromo-2-phenylacetate

Product 1

HCID 20249493N-[alpha-(t-butoxycarbonyl) benzyloxy] phthalimideYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(a)(i) A mixture of N-hydroxyphthalimide (24.5 g), anhydrous potassium carbonate (16.5 g), t-butyl α-bromophenylacetate (41 g) and dimethylsulphoxide (225 ml) was stirred for 18 hours and was then poured into water (1.2 liters). The precipitated solid was filtered off, washed well with water, dried, and crystallised from industrial methylated spirits to give N-[α-(t-butoxycarbonyl) benzyloxy] phthalimide (41 g, 78%); m.p. 120.6°-121.5°.

Workup

  1. filtrationThe precipitated solid was filtered off
  2. washwashed well with water
  3. customdried
  4. customcrystallised from industrial methylated spirits

Sources & evidence

ORD record
ord-3d935ac20a864332b69ef0a12b4ac9f2
Source dataset
uspto-grants-1979_03
Patent number
US04144393

Reaction notes

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