Phthalimide potassium salt → HCID 7571580, compound

HRID 615620Notes

Reaction equation

HRID 615620 reaction equation
BrCCC1C(Cl)=CC(Cl)=[CH:6][C:5]=1[O:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[C:14]=1CCBr.[C:24]1(=[O:34])[NH:28][C:27](=[O:29])[C:26]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:25]12.[K]>CN(C)C=O>[Cl:19][C:17]1[CH:18]=[C:13]([CH:14]=[C:15]([Cl:20])[CH:16]=1)[O:12][CH2:5][CH2:6][N:28]1[C:24](=[O:34])[C:25]2[C:26](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:27]1=[O:29]

Participants

4

Reactant 2

HCID 24194345Phthalimide potassium saltHCID 86739921HCID 86739921, compound

Product 1

HCID 7571580HCID 7571580, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 101.88 g (0.38 mole) of 2-bromoethyl-3,5-dichlorophenyl ether and 70.3 g (0.38 mole) of potassium phthalimide in 800 ml of dimethylformamide was stirred overnight at 85° C. The reaction mixture was filtered and dimethylformamide removed from the filtrate in a rotary evaporator to yield a white solid. The solid was triturated with diethyl ether and the mixture filtered. The solid was dried in vacuo. Recrystallized from methylene chloride-hexane, the product melted at 133+-136° C. Yield overall was 41.7%.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customdimethylformamide removed from the filtrate in a rotary evaporator
  3. customto yield a white solid
  4. customThe solid was triturated with diethyl ether
  5. filtrationthe mixture filtered
  6. customThe solid was dried in vacuo
  7. customRecrystallized from methylene chloride-hexane
  8. customYield overall

Sources & evidence

ORD record
ord-c9ec57bc1d4a477abdcedb80bdb72f41
Source dataset
uspto-grants-1985_02
Patent number
US04500529

Reaction notes

Loading…