3-Chloro-2-methylaniline → HCID 3450994, compound

HRID 1009460Notes

Reaction equation

HRID 1009460 reaction equation
[Cl:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>N1C=CC=CC=1>[Cl:1][C:2]1[C:3]([CH3:9])=[C:4]([NH:5][S:16]([C:13]2[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=2)(=[O:18])=[O:17])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 68943-Chloro-2-methylanilineHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 3450994HCID 3450994, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

18.7 g of 3-chloro-2-methylaniline was dissolved in 120 mL of pyridine, and 22.9 g of p-toluene sulfonylchloride was added portionwise thereto over 30 minutes, followed by stirring at room temperature overnight. The reaction liquid was concentrated under reduced pressure, and to the obtained residue was added water, followed by extraction with ethyl acetate. The organic layer was washed with 1 M hydrochloric acid, saturated brine, an aqueous saturated sodium hydrogen carbonate solution, and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain 34.6 g of N-(3-chloro-2-methylphenyl)-4-methylbenzenesulfonamide.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. additionto the obtained residue was added water
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with 1 M hydrochloric acid, saturated brine
  6. dry with materialan aqueous saturated sodium hydrogen carbonate solution, and saturated brine, and then dried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6aa76b33516545a6b3754800a0f6d403
Source dataset
uspto-grants-2011_07
Patent number
US07973078B2

Reaction notes

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