1-Bromo-4-fluorobutane → 7-Chloro-4-(4-fluorobutyl)-4H-1,2,4-benzothiadiazine 1,1-dioxide

HRID 915742

Reaction equation

HRID 915742 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]2[NH:6][CH:7]=[N:8][S:9](=[O:11])(=[O:10])[C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:21][CH2:22][CH2:23][CH2:24][F:25]>C(#N)C>[Cl:1][C:2]1[CH:13]=[CH:12][C:5]2[N:6]([CH2:21][CH2:22][CH2:23][CH2:24][F:25])[CH:7]=[N:8][S:9](=[O:11])(=[O:10])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 100221-Bromo-4-fluorobutaneHCID 11430Potassium CarbonateHCID 100362767-Chloro-4H-benzo[e][1,2,4]thiadiazine 1,1-dioxide

Product 1

HCID 694152107-Chloro-4-(4-fluorobutyl)-4H-1,2,4-benzothiadiazine 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

150 mg of the compound obtained in Step A of Example 1 are dissolved in 8 ml of acetonitrile, to which 300 mg of K2CO3 and 0.15 ml of 1-bromo-4-fluorobutane are added. The reaction mixture is introduced into a sealed autoclave and is heated at 100° C. for 3 hours. After cooling, the solvent is evaporated off under reduced pressure and the residue is taken up in a minimum of water. The insoluble material is collected by filtration, washed with water and dried. The precipitate is then recrystallised from a minimum of ethyl acetate with the aid of heat. After cooling, the title compound is collected by filtration, washed with a minimum of ethyl acetate and dried.

Workup

  1. additionare added
  2. additionThe reaction mixture is introduced into a sealed autoclave
  3. temperatureAfter cooling
  4. customthe solvent is evaporated off under reduced pressure
  5. filtrationThe insoluble material is collected by filtration
  6. washwashed with water
  7. customdried
  8. customThe precipitate is then recrystallised from a minimum of ethyl acetate with the aid
  9. temperatureof heat
  10. temperatureAfter cooling
  11. filtrationthe title compound is collected by filtration
  12. washwashed with a minimum of ethyl acetate
  13. customdried

Sources & evidence

ORD record
ord-d4f40c2eb7f745509f9fcd77489c0491
Source dataset
uspto-grants-2007_09
Patent number
US07268129B2

Linked notes

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