1-Bromo-2-Chloroethane → 2-(2-chloroethyl)-3,4-dihydro-2H-1,2-benzothiazin-4-one 1,1-dioxide ethylene acetal

HRID 611498Notes

Reaction equation

HRID 611498 reaction equation
[H-].[Na+].[CH2:3]1[O:18][C:6]2([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[S:9](=[O:17])(=[O:16])[NH:8][CH2:7]2)[O:5][CH2:4]1.Br[CH2:20][CH2:21][Cl:22]>CN(C=O)C>[CH2:3]1[O:18][C:6]2([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[S:9](=[O:17])(=[O:16])[N:8]([CH2:20][CH2:21][Cl:22])[CH2:7]2)[O:5][CH2:4]1

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 24758Sodium hydrideHCID 218178932H-1,2-benzothiazin-4(3H)-one 1,1-dioxide ethylene ketal

Product 1

HCID 121117392-(2-chloroethyl)-3,4-dihydro-2H-1,2-benzothiazin-4-one 1,1-dioxide ethylene acetal

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of 440 mg (11 mmol) of 60% sodium hydride in 20 ml of DMF, a solution of 2.41 g (10 mmol) of 3,4-dihydro-2H-1,2-benzothiazin-4-one 1,1-dioxide ethylene acetal in 10 ml of DMF was added under ice cooling and stirring. The reaction mixture was stirred for one hour at 0° C. and then for further one hour at room temperature. Under ice cooling, a solution of 2.86 g (20 mmol) of 1-bromo-2-chloroethane in 10 ml of DMF was added to the reaction mixture, followed by stirring for 16 hours at room temperature.

Workup

  1. stirringThe reaction mixture was stirred for one hour at 0° C.
  2. stirringby stirring for 16 hours at room temperature

Sources & evidence

ORD record
ord-cf1cfc4ae7aa4d2984fbf1e003083ec9
Source dataset
uspto-grants-1999_12
Patent number
US06001827

Reaction notes

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