Water → 2-[(2,5-Diphenyl-1,3-oxazol-4-yl)methyl]-1H-isoindole-1,3(2H)-dione

HRID 236536Notes

Reaction equation

HRID 236536 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].Cl[CH2:14][C:15]1[N:16]=[C:17]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:18][C:19]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CN(C)C=O>[C:1]1(=[O:11])[N:5]([CH2:14][C:15]2[N:16]=[C:17]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:18][C:19]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12

Participants

5

Reactant 3

HCID 962WaterHCID 109235994-(Chloromethyl)-2,5-diphenyloxazoleHCID 24194345Phthalimide potassium salt

Product 1

HCID 151064332-[(2,5-Diphenyl-1,3-oxazol-4-yl)methyl]-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of potassium phthalimide (10 g, 54 mmoles) and 4-chloromethyl-2,5-diphenyloxazole (10.4 g, 40 mmoles) in 80 cc of dimethylformamide was heated at 100° C. for 2 hours. When the solution was cooled to room temperature 300 cc of water was added. The solution was extracted with chloroform several times. The combined chloroform solution was washed with 20-30 ml of 0.2N sodium hydroxide and finally with water. After drying over sodium sulfate the chloroform was concentrated. The product precipitated out.

Workup

  1. additionwas added
  2. extractionThe solution was extracted with chloroform several times
  3. washThe combined chloroform solution was washed with 20-30 ml of 0.2N sodium hydroxide and finally with water
  4. dry with materialAfter drying over sodium sulfate the chloroform
  5. concentrationwas concentrated
  6. customThe product precipitated out

Sources & evidence

ORD record
ord-fc0cb53232d64b40b80fc1ba06ee29bb
Source dataset
uspto-grants-1987_02
Patent number
US04645618

Reaction notes

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