Pyridine → HCID 3288660, compound

HRID 1776606Notes

Reaction equation

HRID 1776606 reaction equation
[CH3:1][S:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.C(Cl)Cl.N1C=CC=CC=1.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>Cl>[CH3:1][S:2][C:3]1[CH:9]=[CH:8][C:6]([NH:7][S:20]([CH3:19])(=[O:22])=[O:21])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 660384-(Methylthio)aniline

Product 1

HCID 3288660HCID 3288660, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

4-(methylthio)aniline (500 mg, 3.59 mmol) was dissolved in DCM (10 ml, 155 mmol). Pyridine (1 ml, 12.36 mmol) and methanesulfonyl chloride (0.336 ml, 4.31 mmol) were added, and the reaction was stirred at RT for 3 hours to achieve completion. The reaction mixture was diluted with HCl 1N and extracted with DCM. The organic phase was dried over Na2SO4 and concentrated under vacuum. The crude product was triturated in Petroleum Ether to give N-(4-(methylthio)phenyl)methanesulfonamide (550 mg, 70.5% yield).

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. customThe crude product was triturated in Petroleum Ether

Sources & evidence

ORD record
ord-195b3edab5a74d48ae9173f960357639
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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