Benzil-di(beta-bromoethyl)ketal → Benzil-di(beta-succinimidoethyl)ketal

HRID 435176Notes

Reaction equation

HRID 435176 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]([O:20][CH2:21][CH2:22]Br)([C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:24]1(=[O:30])[NH:28][C:27](=[O:29])[CH2:26][CH2:25]1.[Na]>CN(C)C=O>[C:27]1(=[O:29])[N:28]([CH2:2][CH2:3][O:4][C:5]([O:20][CH2:21][CH2:22][N:28]2[C:24](=[O:30])[CH2:25][CH2:26][C:27]2=[O:29])([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:13])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:24](=[O:30])[CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 2326685Benzil-di(beta-bromoethyl)ketalHCID 66769941Sodium succinimide

Product 1

HCID 20440910Benzil-di(beta-succinimidoethyl)ketalYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

One hundred (100) grams of benzil-di(β-bromoethyl)ketal and 60.5 g of sodium succinimide were dissolved in 500 ml of N,N-dimethylformamide (to be referred to as DMF), and the solution was heated at 50° to 60° C. for 6 hours with stirring. After the reaction, the reaction mixture was poured into 1 liter of ice water. The resulting crystals were filtered, thoroughly washed with water, and dried to afford 95 g (88% yield) of benzil-di(β-succinimidoethyl)ketal as white crystals. Recrystallization from ethanol yielded crystals having a melting point of 90° to 92° C. The product is referred to as initiator 1.

Workup

  1. temperaturethe solution was heated at 50° to 60° C. for 6 hours
  2. customAfter the reaction
  3. filtrationThe resulting crystals were filtered
  4. washthoroughly washed with water
  5. customdried

Sources & evidence

ORD record
ord-5529adb193a54c74bb4a31deceb29d37
Source dataset
uspto-grants-1983_08
Patent number
US04400519

Reaction notes

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