Benzyl Chloride → Benzylsuccinamate

HRID 1576879Notes

Reaction equation

HRID 1576879 reaction equation
[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][C:4]([NH2:6])=[O:5].[CH2:9](Cl)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C>CN(C)C=O>[C:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:7])[CH2:2][CH2:3][C:4]([NH2:6])=[O:5]

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 8471TriethylamineHCID 12522Succinamic acid

Product 1

HCID 21470073Benzylsuccinamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 23.4 g. (0.20 mole) of succinamic acid, 25.4 g. (0.20 mole) of benzyl chloride, 20.2 g. (0.20 mole) triethylamine and 250 ml. dimethylformamide is stirred at 95°C. for 20 hours. The reaction mixture is diluted with 500 ml. water and the product extracted into two 200 ml. portions of ethyl ether. The combined ether extracts are washed with two 50 ml. portions of saturated sodium bicarbonate solution, then two 50 ml. portions of water and dried over anhydrous magnesium sulfate. After filtering, the solution is concentrated at 15 - 20 mm. and 40°C. to give benzyl succinamate.

Workup

  1. additionA mixture of 23.4 g
  2. additionThe reaction mixture is diluted with 500 ml
  3. extractionwater and the product extracted into two 200 ml
  4. washThe combined ether extracts are washed with two 50 ml
  5. dry with materialportions of water and dried over anhydrous magnesium sulfate
  6. filtrationAfter filtering
  7. concentrationthe solution is concentrated at 15 - 20 mm

Sources & evidence

ORD record
ord-620d40c5a8ff4d49aa90cd432716a964
Source dataset
uspto-grants-1976_09
Patent number
US03983138

Reaction notes

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