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

HRID 839452Notes

Reaction equation

HRID 839452 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 (24.5g), anhydrous potassium carbonate (16.5g), t-butyl α-bromophenylacetate (41g) 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 (41g, 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-0aecb8d15e0f42cb9b1ed08a1c512a32
Source dataset
uspto-grants-1978_06
Patent number
US04095021

Reaction notes

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