Hydrochloric Acid → Pentachlorothiophenol

HRID 1462967

Reaction equation

HRID 1462967 reaction equation
[Cl:1][C:2]1[C:7](Cl)=[C:6]([Cl:9])[C:5]([Cl:10])=[C:4]([Cl:11])[C:3]=1[Cl:12].[SH-:13].[Na+].[OH-].[Na+].Cl>O.CN(C)C=O>[Cl:1][C:2]1[C:7]([SH:13])=[C:6]([Cl:9])[C:5]([Cl:10])=[C:4]([Cl:11])[C:3]=1[Cl:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8370HexachlorobenzeneHCID 14798Sodium HydroxideHCID 28015Sodium hydrosulfide

Product 1

HCID 8620Pentachlorothiophenol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

Hexachlorobenzene (25.0 g, 0.088 mol) was added to 50 mL of dimethylformamide followed by the addition of 7.4 g (0.096 mol) of 73% sodium hydrosulfide and 7.9 mL (0.079 mol) of 40% aqueous sodium hydroxide. The stirred reaction mixture was heated to 85° C. for 3.0 hr, cooled to room temperature, and poured into 200 mL of water. After 10 min of stirring, the insoluble material was removed by filtration, and the filtrate acidified with 15 mL (0.18 mol) of concentrated aqueous hydrochloric acid. The resulting precipitate was collected by filtration, washed with 100 mL of water, and dried in vacuo giving 22.8 g, 92% of theoretical, of pentachlorothiophenol.

Workup

  1. customThe stirred reaction mixture
  2. temperaturecooled to room temperature
  3. customthe insoluble material was removed by filtration
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with 100 mL of water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-da1d455dfb354f818f19e32c4c1d6b7b
Source dataset
uspto-grants-1984_07
Patent number
US04461918

Linked notes

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