Sodium Sulfide → Bis(2,6-dichlorobenzyl) sulfide

HRID 6286

Reaction equation

HRID 6286 reaction equation
[S-2:1].[Na+].[Na+].[Cl:4][C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:6]=1[CH2:7]Cl>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[Cl:4][C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:6]=1[CH2:7][S:1][CH2:7][C:6]1[C:5]([Cl:4])=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:13]

Participants

5

Reactant 2

HCID 14804Sodium SulfideHCID 748322,6-Dichlorobenzyl chloride

Product 1

HCID 20404720Bis(2,6-dichlorobenzyl) sulfideYield 80.4%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

A mixture of 98.8 g (0.411 mol) of sodium sulfide, 5.0 g of tetrabutylammonium hydrogen sulfate and 110 ml of water are stirred in a reaction vessel equipped with a stirrer, thermometer and heatable dropping funnel, until a solution is obtained. 107.2 g of melted 2,6-dichlorobenzyl chloride are added with vigorous stirring over a period of 25 minutes at such a rate that the inside temperature does not exceed 55° C. The reaction mixture is worked up as in Example 9a) to give 77.6 g (80% of theory) of bis(2,6-dichlorobenzyl) sulfide in the form of white crystals of melting point 128°-130° C.

Workup

  1. customequipped with a stirrer
  2. customuntil a solution is obtained
  3. stirringwith vigorous stirring over a period of 25 minutes at such a rate that the inside temperature
  4. customdoes not exceed 55° C

Sources & evidence

ORD record
ord-36a943ae44634d7499c53401c1d522ef
Source dataset
uspto-grants-1993_09
Patent number
US05247113

Linked notes

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