Hydrochloric Acid → N-(3,5-Dimethylphenylthio)succinimide

HRID 50034

Reaction equation

HRID 50034 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([SH:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.Cl[N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C:12]1=[O:17].C(N(CC)CC)C.Cl>ClCCl>[CH3:1][C:2]1[CH:3]=[C:4]([S:9][N:11]2[C:15](=[O:16])[CH2:14][CH2:13][C:12]2=[O:17])[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31398Chlorosuccinimide2×HCID 1175483,5-Dimethylbenzenethiol

Product 1

HCID 11053620N-(3,5-Dimethylphenylthio)succinimideYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3,5-Dimethylthiophenol (2.76 g, 0.02 mol) was added by a syringe to an ice cooled mixture of N-chlorosuccinimide (3.34 g, 0.025 mol) and anhydrous dichloromethane (30 mL) under argon atmosphere. After 1 hour, N-chlorosuccinimide (0.4 g, 0.003 mol) was added, then reaction was stirred for 2.5 hours. Triethylamine (3.9 mL, 0.028 mol) was added while stirring for 15 minutes, then dichloromethane and 1N HCl were added. After shaking, organic layer was dried, concentrated to a small volume and passed through a Celite® column. After evaporation of the solvent, the residue was triturated with diethyl ether to give 3.0 g (64%) of title compound, mp 131-134° C. (from diethyl ether).

Workup

  1. temperaturecooled
  2. customreaction
  3. stirringwhile stirring for 15 minutes
  4. stirringAfter shaking
  5. customorganic layer was dried
  6. concentrationconcentrated to a small volume
  7. customAfter evaporation of the solvent
  8. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-9d4465c4676042c4a40a89baa0810587
Source dataset
uspto-grants-2004_03
Patent number
US06710068B2

Linked notes

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