Hydrochloric Acid → 3-Chloro-2-(2,4-dichlorophenylthio)-n-methyl-sulphonyl-aniline

HRID 379084Notes

Reaction equation

HRID 379084 reaction equation
[Cl:1][C:2]1[C:3]([S:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[S:18](Cl)([OH:21])(=O)=[O:19].[CH4:23].O.Cl>N1C=CC=CC=1>[Cl:1][CH:2]1[C:8](=[S:18](=[O:21])=[O:19])[CH:7]=[CH:6][C:4]([NH:5][CH3:23])=[C:3]1[S:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[Cl:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 19821184Methane sulfochlorideHCID 216978693-Chloro-2-(2,4-dichlorophenylthio)-aniline

Product 1

HCID 882331553-Chloro-2-(2,4-dichlorophenylthio)-n-methyl-sulphonyl-aniline

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-chloro-2-(2,4-dichlorophenylthio)-aniline (8.96 g) is dissolved in pyridine (300 ml). Methane sulphochloride (4.56 ml) is added dropwise to this solution and the resulting mixture is stirred for 12 hours at room temperature. Following this, the mixture is emptied onto iced water, acidified with concentrated hydrochloric acid. The resulting mixture is extracted 3 times with methylene chloride (each 200 ml). The combined organic phases are dried (Na2SO4), filtered and the filtrate is concentrated in a vacuum. The resulting residue is dissolved in methanol, mixed with a sodium methylate solution in methanol (29.7%, 50 ml) and is stirred for 12 hours. The clear solution is acidified with concentrated hydrochloric acid, brought to room temperature, diluted with water (200 ml). The result in precipitate is suction filtered, washed with water and dried. Yield: 10.69 g (95.0%).

Workup

  1. extractionThe resulting mixture is extracted 3 times with methylene chloride (each 200 ml)
  2. dry with materialThe combined organic phases are dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationthe filtrate is concentrated in a vacuum
  5. dissolutionThe resulting residue is dissolved in methanol
  6. additionmixed with a sodium methylate solution in methanol (29.7%, 50 ml)
  7. stirringis stirred for 12 hours
  8. custombrought to room temperature
  9. additiondiluted with water (200 ml)
  10. customThe result in precipitate
  11. filtrationfiltered
  12. washwashed with water
  13. customdried

Sources & evidence

ORD record
ord-609367304745452494cbf0898a405304
Source dataset
uspto-grants-2001_10
Patent number
US06297282B1

Reaction notes

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