Water → 9-(4-Butoxyphenyl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

HRID 1405895Notes

Reaction equation

HRID 1405895 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:13]([NH2:18])=[N:14][CH:15]=[CH:16][CH:17]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].Cl[CH2:22][CH2:23][S:24](Cl)(=[O:26])=[O:25].O>C1COCC1.CCCCCC>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:13]3=[N:18][S:24](=[O:26])(=[O:25])[CH2:23][CH2:22][N:14]3[CH:15]=[CH:16][CH:17]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 667483793-(4-Butoxyphenyl)pyridin-2-amine

Product 1

HCID 667480579-(4-Butoxyphenyl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of 3-(4-butoxyphenyl)pyridin-2-amine (690 mg) in THF (dry) (5 mL) was added to a suspension of NaH (60%, 569 mg) and 2-chloroethanesulfonyl chloride (0.893 mL) in THF (dry) (5 mL) at 0° C. The mixture was stirred at room temperature overnight. Water and hexane were added to give a white precipitate. The precipitate was collected by filtration and washed with water and EtOAc, and then recrystallized from IPE-EtOH to give the title compound (502 mg) as a white solid.

Workup

  1. customto give a white precipitate
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water and EtOAc
  4. customrecrystallized from IPE-EtOH

Sources & evidence

ORD record
ord-dbbbcc99dc984ef785343db95ae7fb2f
Source dataset
uspto-grants-2014_12
Patent number
US08916551B2

Reaction notes

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