Hydrochloric Acid → 3-Chloro-2-methylbenzenesulfonyl chloride

HRID 1995390Notes

Reaction equation

HRID 1995390 reaction equation
[Cl:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)N.[ClH:10].N([O-])=O.[Na+].O.O.O.O.O.O.[Cl-].[Mg+2].[Cl-].[S:24](=[O:26])=[O:25]>O.C(O)(=O)C.[Cu](Cl)Cl>[Cl:1][C:2]1[C:3]([CH3:9])=[C:4]([S:24]([Cl:10])(=[O:26])=[O:25])[CH:6]=[CH:7][CH:8]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 68943-Chloro-2-methylanilineHCID 24644Magnesium chloride hexahydrateHCID 23668193Sodium Nitrite

Product 1

HCID 5227343-Chloro-2-methylbenzenesulfonyl chloride

Reagents, catalysts & solvents 3

HCID 24014Cupric ChlorideCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

30 gm (0.212 mol) of 3-chloro-2-methyl-aniline were admixed with 50 ml of concentrated aqueous hydrochloric acid. The reaction mixture was cooled to between -7° and -3° C. and at this temperature a solution of 14.6 gm (0.212 mol) of sodium nitrite in 50 ml of water was added dropwise thereto over a period of 1 hour. After stirring for a further hour at 0° C., 20.3 gm (0.1 mol) of magnesium chloride hexahydrate were added, and the reaction mixture was stirred for 10 minutes and then filtered. The filtrate was poured into a suspension of 12 gm (71 mmols) of copper (II)chloride in 250 ml of a 30% solution of sulfur dioxide in glacial acetic acid. During the addition the temperature of the reaction mixture rose from 20° C. to 40° C., accompanied by a strong evolution of gas. After stirring for 60 minutes at room temperature and for 60 minutes at 35° C., 500 gm of ice were added. The mixture was stirred until the ice had melted, and then filtered.

Workup

  1. additionwas added dropwise
  2. stirringthe reaction mixture was stirred for 10 minutes
  3. filtrationfiltered
  4. additionDuring the addition the temperature of the reaction mixture
  5. customrose from 20° C. to 40° C.
  6. stirringAfter stirring for 60 minutes at room temperature and for 60 minutes at 35° C.
  7. filtrationfiltered

Sources & evidence

ORD record
ord-1506d1b6c55540faabc9f62a2dc977fc
Source dataset
uspto-grants-1983_09
Patent number
US04404230

Reaction notes

Loading…