1-Bromo-2-Chloroethane → HCID 22595755, compound

HRID 1760529Notes

Reaction equation

HRID 1760529 reaction equation
[H-].[Na+].[CH3:3][CH:4]([N:6]1[CH2:11][C:10]2[CH:12]=[C:13]([S:16][CH3:17])[CH:14]=[CH:15][C:9]=2[NH:8][S:7]1(=[O:19])=[O:18])[CH3:5].[H][H].Br[CH2:23][CH2:24][Cl:25]>CN(C=O)C.CCCCCC>[Cl:25][CH2:24][CH2:23][N:8]1[C:9]2[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][C:10]=2[CH2:11][N:6]([CH:4]([CH3:3])[CH3:5])[S:7]1(=[O:19])=[O:18]

Participants

7

Reactant 4

HCID 78491-Bromo-2-ChloroethaneHCID 24758Sodium hydrideHCID 22595747HCID 22595747, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22595755HCID 22595755, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

To a 250 ml 3 necked flask equipped thermometer, pressure equalised dropping funnel, nitrogen bubbler and magnetic stirrer bar was added 60% sodium hydride (1.77 g, 1.062 g, 0.04425 mol,) hexane washed, to dry DMF (75 ml). To this stirred suspension was added dropwise a solution of 3,4-dihydro-3-(1-methylethyl)-6-methylthio-1H-2,1,3-benzothiadiazine-2,2-dioxide (10.0 g, 0.0368 mol) in dry DMF (75 ml) (slight exotherm). The suspension was stirred under nitrogen for 2 hr until hydrogen evolution ceased. 1-Bromo-2-chloroethane (6.33 g, 3.77 ml, 0.04425 mol) was added dropwise and the reaction mixture allowed to stir at room temperature under nitrogen overnight. The reaction mixture was poured onto ice-water (800 ml) with stirring for 1 hr, filtered and washed with water (200 ml) to leave a white solid which was dried in vacuo at 50° C. to give a solid. Mp 74-75° C.

Workup

  1. washwashed, to dry DMF (75 ml)
  2. additionThe reaction mixture was poured onto ice-water (800 ml)
  3. stirringwith stirring for 1 hr
  4. filtrationfiltered
  5. washwashed with water (200 ml)
  6. customto leave a white solid which
  7. customwas dried in vacuo at 50° C.
  8. customto give a solid

Sources & evidence

ORD record
ord-cda12bdccb154b9e9a3d3527ae478fa4
Source dataset
uspto-grants-2005_01
Patent number
US06844338B2

Reaction notes

Loading…