Hydrochloric Acid → 2-Cyanobenzenesulfonyl Chloride

HRID 992474Notes

Reaction equation

HRID 992474 reaction equation
[ClH:1].[C:2]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)N)#[N:3].N([O-])=O.[Na+].[S:15](=[O:17])=[O:16]>C(O)(=O)C.O>[C:2]([C:4]1[CH:5]=[CH:6][CH:8]=[CH:9][C:10]=1[S:15]([Cl:1])(=[O:17])=[O:16])#[N:3]

Participants

7

Reactant 4

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

Product 1

HCID 5223472-Cyanobenzenesulfonyl Chloride

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a mixed solution of 200 ml of water and 250 ml of concentrated hydrochloric acid was added 25.0 g (212 mmol) of 3-cyanoaniline followed by stirring. An aqueous solution (80 ml) of 15.5 g (223 mmol) of sodium nitrite was added dropwise thereinto at −10° C. The reaction solution was added to acetic acid saturated with sulfur dioxide (prepared by saturating sulfur dioxide in 250 ml of acetic acid followed by adding 2.1 g of cuprous chloride) under ice-cooling and stirring. After 1 hour, the reaction solution was poured onto 500 ml of ice water and extracted with diethyl ether. The extract was washed with a saturated aqueous solution of sodium bicarbonate, water and brine successively, and dried over magnesium sulfate. The solvent was evaporated, a mixed solution of diethyl ether and hexane was added to the residue and the crystals were collected by filtration to give 16.0 g of the title compound.

Workup

  1. customat −10° C
  2. temperaturecooling
  3. stirringstirring
  4. extractionextracted with diethyl ether
  5. washThe extract was washed with a saturated aqueous solution of sodium bicarbonate, water and brine successively
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated
  8. additiona mixed solution of diethyl ether and hexane was added to the residue
  9. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-4693d3d4b02c45b7b577dcf92d0df510
Source dataset
uspto-grants-2002_10
Patent number
US06469043B1

Reaction notes

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