Triethylamine → p-t-BUTYLPHENYL 1-(p-CHLOROPHENYL SULFONYL)VINYL SULFIDE

HRID 1156389Notes

Reaction equation

HRID 1156389 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([S:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=2)[CH2:12]Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11]([S:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:19][CH:20]=2)=[CH2:12])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 130448072-CHLORO-1-(p-CHLOROPHENYLSULFONYL)ETHYL p-t-BUTYLPHENYL SULFIDE

Product 1

HCID 13044814p-t-BUTYLPHENYL 1-(p-CHLOROPHENYL SULFONYL)VINYL SULFIDEYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

p-t-Butylphenyl 1-(p-chlorophenylsulfonyl)-2-chloroethyl sulfide (16.12 g, 40.0 mmoles) was dissolved in 80 ml of tetrahydrofuran at 25° C. The solution was treated with 5.6 ml (4.08 g, 40.3 mmoles) of triethylamine and allowed to stand for 30 minutes. After filtration had separated the triethylamine hydrochloride, the filtrate was freed of solvent by evaporation at reduced pressure. The residue was a colorless solid, m.p. 74°-79°. Recrystallization from 25 ml of ethanol gave 12.2 g (84%) of pure product m.p. 79°-81°.

Workup

  1. filtrationAfter filtration
  2. customhad separated the triethylamine hydrochloride
  3. customthe filtrate was freed of solvent by evaporation at reduced pressure
  4. customRecrystallization from 25 ml of ethanol

Sources & evidence

ORD record
ord-bf7c901da0f84cb4bcd5d486d4c4cc82
Source dataset
uspto-grants-1982_06
Patent number
US04335142

Reaction notes

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