Water → 9-Bromo-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

HRID 1405648Notes

Reaction equation

HRID 1405648 reaction equation
[Br:1][C:2]1[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][CH:7]=1.Cl[CH2:10][CH2:11][S:12](Cl)(=[O:14])=[O:13].[H-].[Na+].O>C1COCC1>[Br:1][C:2]1[C:3]2=[N:8][S:12](=[O:14])(=[O:13])[CH2:11][CH2:10][N:4]2[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 8177002-Amino-3-bromopyridine

Product 1

HCID 667481039-Bromo-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxideYield 74.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A mixture of 3-bromopyridin-2-amine (3 g) in dehydrated THF (30 mL) was added to a mixture of 2-chloroethanesulfonyl chloride (7.07 g) and sodium hydride (60%, 3.47 g) in dehydrated THF (30 mL) at room temperature, and the reaction mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and THF was removed under reduced pressure. The resulting precipitate was collected by filtration, and washed with water and diethyl ether to give the title compound (3.41 g) as a white solid.

Workup

  1. customwas removed under reduced pressure
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water and diethyl ether

Sources & evidence

ORD record
ord-3329c9fdb46e4f2892fbcec23002a3d8
Source dataset
uspto-grants-2014_12
Patent number
US08916551B2

Reaction notes

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