2-Bromoethanol → 2-(7-Methoxy-1,1-dioxido-4H-1,2,4-benzothiadiazin-4-yl)ethanol

HRID 915738Notes

Reaction equation

HRID 915738 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[NH:7][CH:8]=[N:9][S:10](=[O:12])(=[O:11])[C:5]=2[CH:4]=1.[F-].[Cs+].Br[CH2:18][CH2:19][OH:20]>CN(C=O)C.CC#N>[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[N:7]([CH2:18][CH2:19][OH:20])[CH:8]=[N:9][S:10](=[O:12])(=[O:11])[C:5]=2[CH:4]=1

Participants

6

Reactant 3

HCID 108982-Bromoethanol3×HCID 25953Cesium fluoride2×HCID 574238877-methoxy-4H-1,2,4-benzothiadiazine 1,1-dioxide

Product 1

HCID 694593512-(7-Methoxy-1,1-dioxido-4H-1,2,4-benzothiadiazin-4-yl)ethanol

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 7-methoxy-4H-1,2,4-benzothiadiazine 1,1-dioxide (4.0 g, 18.8 mmol) in a mixture of 30 ml of DMF and 30 ml of CH3CN there are added 8.6 g (56.6 mmol) of CsF and 1.47 ml (18.8 mmol) of 2-bromoethanol. Stirring is carried out for 2 hours at 75° C. and 1.47 ml (18.8 mmol) of 2-bromoethanol are added. After 6 more hours at 75° C., a further 1.47 ml (18.8 mmol) of 2-bromoethanol and then 2.8 g (18.8 mmol) of CsF are added and stirring is continued at 75° C. overnight. The salts are filtered off at ambient temperature and rinsed with CH3CN; the filtrate is evaporated to dryness. The residue is taken up in CH2Cl2, and the organic phase is washed with saturated NaCl solution and dried (MgSO4). After evaporation, the sticky residue is taken up in a mixture of ethyl ether/CH2Cl2. The gum is triturated until a solid is obtained, which is filtered off to obtain the title compound.

Workup

  1. stirringstirring
  2. waitis continued at 75° C. overnight
  3. filtrationThe salts are filtered off at ambient temperature
  4. washrinsed with CH3CN
  5. customthe filtrate is evaporated to dryness
  6. washthe organic phase is washed with saturated NaCl solution
  7. dry with materialdried (MgSO4)
  8. customAfter evaporation
  9. additionthe sticky residue is taken up in a mixture of ethyl ether/CH2Cl2
  10. customThe gum is triturated until a solid
  11. customis obtained
  12. filtrationwhich is filtered off

Sources & evidence

ORD record
ord-36bdac7bd5544f92b5aa051e03023ff5
Source dataset
uspto-grants-2007_09
Patent number
US07268130B2

Reaction notes

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