Hydrochloric Acid → 3-Cyanobenzene-1-sulfonyl chloride

HRID 1173088Notes

Reaction equation

HRID 1173088 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)N)#[N:2].[ClH:10].N([O-])=O.[Na+].[S:15](=[O:17])=[O:16]>O>[C:1]([C:3]1[CH:4]=[C:5]([S:15]([Cl:10])(=[O:17])=[O:16])[CH:7]=[CH:8][CH:9]=1)#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 167023-AminobenzonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 28013603-Cyanobenzene-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

25.0 g (212 mmol) of 3-cyanoaniline was added to a mixed solution of 200 ml of water and 250 ml of concentrated hydrochloric acid and the mixture was stirred. An aqueous solution (80 ml) containing 15.5 g (223 mmol) of sodium nitrite was added dropwise into the mixture at −10° C. The reaction solution was added to a sulfur dioxide saturated acetic acid solution (solution prepared by saturating 250 ml of acetic acid with sulfur dioxide and then adding 2.1 g of cuprous chloride thereto) under ice-cooling with stirring. After one hour, the reaction solution was poured into 500 ml of ice-water and extracted with diethyl ether. The extract was successively washed with an aqueous saturated sodium bicarbonate, water and brine, and dried over magnesium sulfate. The solvent was evaporated, and to the residue was added a mixed solution of diethyl ether and hexane. The crystals were collected by filtration, to give 16.0 g of the title compound.

Workup

  1. additionwas added dropwise into the mixture at −10° C
  2. customprepared
  3. concentrationby saturating 250 ml of acetic acid with sulfur dioxide
  4. additionadding 2.1 g of cuprous chloride
  5. temperature) under ice-cooling
  6. stirringwith stirring
  7. additionthe reaction solution was poured into 500 ml of ice-water
  8. extractionextracted with diethyl ether
  9. washThe extract was successively washed with an aqueous saturated sodium bicarbonate, water and brine
  10. dry with materialdried over magnesium sulfate
  11. customThe solvent was evaporated
  12. additionto the residue was added a mixed solution of diethyl ether and hexane
  13. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-fd93ad0307c14b96b7a70f25d8d4d3f3
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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