Hydrochloric Acid → 3-Methoxybenzenesulfonyl chloride

HRID 1995398Notes

Reaction equation

HRID 1995398 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5](N)[CH:4]=1.[ClH:10].N([O-])=O.[Na+].[S:15](=[O:17])=[O:16]>C(O)(=O)C.O.C1C=CC=CC=1.[Cu](Cl)Cl.[Cu]Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:15]([Cl:10])(=[O:17])=[O:16])[CH:6]=[CH:7][CH:8]=1

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 108243-MethoxyanilineHCID 23668193Sodium Nitrite

Product 1

HCID 27375043-Methoxybenzenesulfonyl chloride

Reagents, catalysts & solvents 5

HCID 24014Cupric ChlorideCatalystHCID 62652Cuprous chlorideCatalystHCID 176Acetic AcidSolvent2×HCID 241BenzeneSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

61.6 gm (0.5 mol) of m-anisidine were dissolved in 50 ml of glacial acetic acid, and the solution was admixed dropwise with 110 ml of concentrated aqueous hydrochloric acid. The mixture was cooled to 0° C. and diazotized with a solution of 38 gm (0.551 mol) of sodium nitrite in 75 ml of water. After stirring for 10-15 minutes, the reaction mixture was poured slowly to a mixture of 24 gm (0.14 mol) of copper (II) chloride, 5 gm of copper(I)chloride, 300 ml of a 30% solution of sulfur dioxide in glacial acetic acid and 450 ml of benzene, whereby a strong evolution of gas and an increase in the temperature up to 40° C. was observed. As soon as the reaction temperature dropped, the mixture was heated for 1 hour at 40° C. After cooling, the reaction mixture was diluted with 2.5 liters of ice water, filtered and the organic phase was separated. The organic phase was washed with water and sodium bicarbonate solution and evaporated.

Workup

  1. temperaturean increase in the temperature up to 40° C.
  2. additionAs soon as the reaction temperature dropped
  3. temperaturethe mixture was heated for 1 hour at 40° C
  4. temperatureAfter cooling
  5. filtrationfiltered
  6. customthe organic phase was separated
  7. washThe organic phase was washed with water and sodium bicarbonate solution
  8. customevaporated

Sources & evidence

ORD record
ord-cac0b4b308bd484cb765d5260a14fa7a
Source dataset
uspto-grants-1983_09
Patent number
US04404230

Reaction notes

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