Dimethylamine → 6-chloro-N,N-dimethylpyridine-3-sulfonamide

HRID 45222Notes

Reaction equation

HRID 45222 reaction equation
[CH3:1][NH:2][CH3:3].[Cl:4][C:5]1[N:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1>C1COCC1.CCOC(C)=O>[Cl:4][C:5]1[N:10]=[CH:9][C:8]([S:11]([N:2]([CH3:3])[CH3:1])(=[O:13])=[O:12])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 27927922-Chloro-5-pyridinesulfonyl chloride

Product 1

HCID 47298556-chloro-N,N-dimethylpyridine-3-sulfonamideYield 93%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 4.7 mL (9.43 mmol) of dimethylamine (2N in THF) and 2.6 mL (18.86 mmol) of TEA in 20 mL of THF is added dropwise, at 0° C., a solution of 2 g (9.43 mmol) of 6-chloropyridine-3-sulfonyl chloride (prepared according to patent WO 9840332) in 5 mL of THF. After stirring for 40 minutes at 0° C., the reaction medium is taken up in 40 mL of EtOAc, washed with water (2×40 mL) and brine (40 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. 1.93 g of 6-chloro-N,N-dimethylpyridine-3-sulfonamide are obtained in the form of a brown solid, which is used without further purification in the following step.

Workup

  1. additionis added dropwise, at 0° C.
  2. washwashed with water (2×40 mL) and brine (40 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b1dea52191164b518b11cf5eb9b6b959
Source dataset
uspto-grants-2013_09
Patent number
US08541455B2

Reaction notes

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