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

HRID 2268782Notes

Reaction equation

HRID 2268782 reaction equation
[CH3:1][CH:2]([N:4]1[CH2:9][C:8]2[CH:10]=[C:11]([S:14][CH3:15])[CH:12]=[CH:13][C:7]=2[N:6]([CH2:16][CH:17]=C)[S:5]1(=[O:20])=[O:19])[CH3:3].[H-].[Na+].CC(N1CC2C=C(SC)C=CC=2NS1(=O)=O)C.[H][H].BrCC[Cl:45]>CN(C=O)C.CCCCCC>[Cl:45][CH2:17][CH2:16][N:6]1[C:7]2[CH:13]=[CH:12][C:11]([S:14][CH3:15])=[CH:10][C:8]=2[CH2:9][N:4]([CH:2]([CH3:3])[CH3:1])[S:5]1(=[O:20])=[O:19]

Participants

8

Reactant 5

HCID 78491-Bromo-2-ChloroethaneHCID 24758Sodium hydrideHCID 22595722HCID 22595722, compoundHCID 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-2425665bb1fe41d9ba59a2c58351b528
Source dataset
uspto-grants-2001_12
Patent number
US06329366B1

Reaction notes

Loading…