Triethylamine → 1-[(1-Phenylethyl)sulfanyl]pyrrolidine-2,5-dione

HRID 1679285

Reaction equation

HRID 1679285 reaction equation
Cl[N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[C:9]1([CH:15]([SH:17])[CH3:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C>C1C=CC=CC=1>[CH3:16][CH:15]([S:17][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 1418501-Phenylethanethiol

Product 1

HCID 205546171-[(1-Phenylethyl)sulfanyl]pyrrolidine-2,5-dioneYield 36.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent4×

Procedure

To a suitable reactor equipped with temperature controlling means and stirring means, there are charged, while maintaining the temperature at about room temperature, N-chlorosuccinimide (about 0.30 mole) in 400 ml of benzene and 1-phenylethanethiol (about 0.30 mole) in 50 ml of benzene. After stirring the reaction mixture 10 minutes, triethylamine (0.32 mole) in 50 ml of benzene is added dropwise. The benzene mixture is stirred one hour and then filtered. The filtrate is washed three times with 250 ml portions of water and then subjected to vacuum with heating to strip off volatile components. A crystalline residue is recrystallized from ethanol to give 26 grams of N-(α-methylbenzylthio)succinimide, m.p. 121-125°C.

Workup

  1. customTo a suitable reactor equipped with temperature
  2. additionare charged
  3. temperaturewhile maintaining the temperature at about room temperature
  4. additionis added dropwise
  5. filtrationfiltered
  6. washThe filtrate is washed three times with 250 ml portions of water
  7. temperaturewith heating
  8. customA crystalline residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-a910ef935e39498f9cd87e7681119e55
Source dataset
uspto-grants-1978_03
Patent number
US04080342

Linked notes

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