Dimethylamine → 2-amino-5-bromo-N,N-dimethylpyridine-3-sulfonamide

HRID 1096801

Reaction equation

HRID 1096801 reaction equation
[NH2:1][C:2]1[C:7]([S:8](Cl)(=[O:10])=[O:9])=[CH:6][C:5]([Br:12])=[CH:4][N:3]=1.[N:13]1[CH:18]=CC=C[CH:14]=1.CNC.C1COCC1>O1CCOCC1>[NH2:1][C:2]1[C:7]([S:8]([N:13]([CH3:18])[CH3:14])(=[O:10])=[O:9])=[CH:6][C:5]([Br:12])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 1049PyridineHCID 8028TetrahydrofuranHCID 533020262-Amino-5-bromopyridine-3-sulfonyl chloride

Product 1

HCID 523351532-amino-5-bromo-N,N-dimethylpyridine-3-sulfonamideYield 55%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a cold (0 □C) suspension of 2-amino-5-bromo-3-pyridinesulfonyl chloride (92.1 mmol) in dry 1,4-dioxane (92 mL) was added pyridine (101.3 mmol) followed by a 2M solution of dimethylamine in THF (101.3 mmol). The reaction was allowed to warm to rt for 2 h, heated to 50 □C for 1 h, then cooled to rt. After standing for 2 h, the precipitate was collected by filtration and rinsed with a minimal amount of cold water. Drying the precipitate to constant weight under high vacuum provided 14.1 g (55%) of the title compound as a white solid. MS(ES)+ m/e 279.8, 282.0 [M+H]+.

Workup

  1. temperatureheated to 50 □C for 1 h
  2. temperaturecooled to rt
  3. filtrationthe precipitate was collected by filtration
  4. washrinsed with a minimal amount of cold water
  5. customDrying the precipitate to constant weight under high vacuum

Sources & evidence

ORD record
ord-3d0dae51816c4e39a2e3d4b71ce2ed83
Source dataset
uspto-grants-2012_03
Patent number
US08138347B2

Linked notes

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