Water → HCID 17777167, compound

HRID 583074Notes

Reaction equation

HRID 583074 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]2[CH2:6][N:7]([CH:12]([CH3:14])[CH3:13])[S:8](=[O:11])(=[O:10])[NH:9][C:4]=2[CH:3]=1.[H-].[Na+].Br[CH2:20][CH2:21][Cl:22].O>CN(C=O)C>[Cl:22][CH2:21][CH2:20][N:9]1[C:4]2[CH:3]=[C:2]([F:1])[CH:16]=[CH:15][C:5]=2[CH2:6][N:7]([CH:12]([CH3:14])[CH3:13])[S:8]1(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 78491-Bromo-2-ChloroethaneHCID 24758Sodium hydrideHCID 17777145HCID 17777145, compound

Product 1

HCID 17777167HCID 17777167, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3,4-dihydro-7-fluoro-3-(1-methylethyl)-1H-2,1,3-benzothiadiazine-2,2-dioxide(1.48 g, 6.07 mmol) in dry DMF (15 ml) was added via a cannula to a flask containing sodium hydride (175 mg, 7.28 mmol) and DMF (2 ml) in Argon atmosphere, and stirred for 2 hours at room temperature when 1-bromo-2-chloroethane (7.28 mmol, 605 μl) was added dropwise. The mixture was stirred overnight at room temperature and water (75 ml) added. The product was extracted with EtOAc (3×50 ml) and the combined organic extracts were washed with water (1×100 ml) and then brine (1×100 ml), dried over sodium sulphate and solvent evaporated at reduced pressure. The residue was purified by flash chromatography on silica gel (EtOAc:Hexanes 1:4) affording pure 1-(2-chloroethyl)-3,4-dihydro-7-fluoro-3-(1-methylethyl)-1H-2,1,3-benzothiadiazine-2,2-dioxide.

Workup

  1. additionwas added dropwise
  2. extractionThe product was extracted with EtOAc (3×50 ml)
  3. washthe combined organic extracts were washed with water (1×100 ml)
  4. dry with materialbrine (1×100 ml), dried over sodium sulphate and solvent
  5. customevaporated at reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (EtOAc:Hexanes 1:4)

Sources & evidence

ORD record
ord-3f299d0a417b41a4981dc790fec14ceb
Source dataset
uspto-grants-1999_07
Patent number
US05929072

Reaction notes

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