Sodium borohydride → HCID 67530154, compound

HRID 17843Notes

Reaction equation

HRID 17843 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]([CH:12]3[CH2:15][CH2:14][CH2:13]3)[CH:7]=[N:8][S:9](=[O:11])(=[O:10])[C:4]=2[CH:3]=1.[BH4-].[Na+]>C(O)(C)C>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]([CH:12]3[CH2:13][CH2:14][CH2:15]3)[CH2:7][NH:8][S:9](=[O:11])(=[O:10])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67530606HCID 67530606, compound

Product 1

HCID 67530154HCID 67530154, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of the 7-chloro-4-cyclobutyl-4H-1,2,4-benzothiadiazine 1,1-dioxide originating from the Step above (3 g) in isopropanol (100 mL) there is added finely ground NaBH4 (2.5 g) and then heating is carried out for 10 minutes at 55° C. The solvent is removed by evaporation under reduced pressure. The residue is taken up in water (100 mL) and brought to acid pH by adding 6N HCl. The title product is extracted with chloroform (3×50 mL). The organic phase is dried over MgSO4 and filtered. The filtrate is evaporated to dryness and the residue is purified by chromatography on a silica column (mobile phase: chloroform). The product obtained is recrystallised from methanol.

Workup

  1. temperatureheating
  2. customThe solvent is removed by evaporation under reduced pressure
  3. additionby adding 6N HCl
  4. extractionThe title product is extracted with chloroform (3×50 mL)
  5. dry with materialThe organic phase is dried over MgSO4
  6. filtrationfiltered
  7. customThe filtrate is evaporated to dryness
  8. customthe residue is purified by chromatography on a silica column (mobile phase: chloroform)
  9. customThe product obtained
  10. customis recrystallised from methanol

Sources & evidence

ORD record
ord-4c5257078e4942ac834ad6a4df35f5d3
Source dataset
uspto-grants-2010_06
Patent number
US07741320B2

Reaction notes

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