Methanesulfonyl chloride → 8-[4-((Methylsulfonyl)amino)phenyl]imidazo[1,2-a]pyridine

HRID 1982541Notes

Reaction equation

HRID 1982541 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[N:10]([CH:14]=[CH:15][N:16]=3)[CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)Cl>[CH3:17][S:18]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]3[N:10]([CH:14]=[CH:15][N:16]=3)[CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1)(=[O:20])=[O:19]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 13810555Benzenamine,4-imidazo[1,2-a]pyridin-8-yl-

Product 1

HCID 138105568-[4-((Methylsulfonyl)amino)phenyl]imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

Dissolve 4 g (19.1 mmol) of the product from Example 20, in 100 ml of methylene chloride and cool to 0° C. Add 1.6 ml of methanesulfonyl chloride slowly, maintaining the temperature at 5° C. Stir at r.t. for 12 hr. Extract the reaction mixture with 100 ml of 10% sodium hydroxide. Wash with 100 ml of methylene chloride and with 100 ml of ether. Treat with charcoal and neutralize with ammonium chloride. The resulting precipitate is filtered and washed with water to provide the title compound.

Workup

  1. extractionExtract the reaction mixture with 100 ml of 10% sodium hydroxide
  2. washWash with 100 ml of methylene chloride and with 100 ml of ether
  3. additionTreat with charcoal
  4. filtrationThe resulting precipitate is filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-910182b2f462405994d37c2bf4e55e6f
Source dataset
uspto-grants-1986_06
Patent number
US04596872

Reaction notes

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