Ethylorthoformate → 6,7-dichloro-4-cyclopropyl-4H-1,2,4-benzothiadiazine 1,1-dioxide

HRID 17836

Reaction equation

HRID 17836 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([S:9]([NH2:12])(=[O:11])=[O:10])=[C:4]([NH:13][CH:14]2[CH2:16][CH2:15]2)[CH:3]=1.[CH:17]([O-])([O-])OCC>>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]2[S:9](=[O:10])(=[O:11])[N:12]=[CH:17][N:13]([CH:14]3[CH2:16][CH2:15]3)[C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 53630039EthylorthoformateHCID 675298334,5-Dichloro-2-cyclopropylaminobenzenesulphonamide

Product 1

HCID 675306506,7-dichloro-4-cyclopropyl-4H-1,2,4-benzothiadiazine 1,1-dioxide

Conditions

Temperature
150 °C

Procedure

In a round-bottom flask, a mixture of 4,5-dichloro-2-cyclopropylaminobenzenesulphonamide from the Step above (2.5 g) and ethyl orthoformate (25 mL) is heated in the open state at 150° C. for 1 hour. The suspension obtained is cooled on an ice bath, and the insoluble material is collected by filtration, washed with ether and dried. The solid is re-dissolved in a mixture of acetone and methanol in the hot state and the hot solution is treated with absorbent carbon and then filtered and concentrated to dryness. The residue is recrystallised from methanol.

Workup

  1. customThe suspension obtained
  2. temperatureis cooled on an ice bath
  3. filtrationthe insoluble material is collected by filtration
  4. washwashed with ether
  5. customdried
  6. dissolutionThe solid is re-dissolved in a mixture of acetone and methanol in the hot state
  7. additionthe hot solution is treated with absorbent carbon
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. customThe residue is recrystallised from methanol

Sources & evidence

ORD record
ord-7b7f45fc90a3465183bb7ac4ccf35df4
Source dataset
uspto-grants-2010_06
Patent number
US07741320B2

Linked notes

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