Sodium borohydride → 6,7-dichloro-4-cyclopropyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide

HRID 17837Notes

Reaction equation

HRID 17837 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:5]([Cl:19])=[CH:6][C:7]2[S:12](=[O:14])(=[O:13])[N:11]=[CH:10][N:9]([CH:15]3[CH2:17][CH2:16]3)[C:8]=2[CH:18]=1>C(O)(C)C>[Cl:3][C:4]1[C:5]([Cl:19])=[CH:6][C:7]2[S:12](=[O:14])(=[O:13])[NH:11][CH2:10][N:9]([CH:15]3[CH2:16][CH2:17]3)[C:8]=2[CH:18]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 675306506,7-dichloro-4-cyclopropyl-4H-1,2,4-benzothiadiazine 1,1-dioxide

Product 1

HCID 446105566,7-dichloro-4-cyclopropyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
52.5 °C

Procedure

Finely ground NaBH4 (1 g) is added to a solution of 6,7-dichloro-4-cyclopropyl-4H-1,2,4-benzothiadiazine 1,1-dioxide from the Step above (1.9 g) in isopropanol (50 mL) and then heated at 50-55° C. for 5-10 minutes. The solvent is removed by evaporation under reduced pressure. The residue is taken up in water (50 mL) and brought to acid pH by adding 6N HCl. The title product is extracted with dichloromethane (3×30 mL). The organic phase is dried over MgSO4 and filtered. The filtrate is evaporated to dryness and the residue obtained is recrystallised from methanol/water 1/1 (60 mL).

Workup

  1. customThe solvent is removed by evaporation under reduced pressure
  2. additionby adding 6N HCl
  3. extractionThe title product is extracted with dichloromethane (3×30 mL)
  4. dry with materialThe organic phase is dried over MgSO4
  5. filtrationfiltered
  6. customThe filtrate is evaporated to dryness
  7. customthe residue obtained
  8. customis recrystallised from methanol/water 1/1 (60 mL)

Sources & evidence

ORD record
ord-a9ab08942b9a49718b6566737d411164
Source dataset
uspto-grants-2010_06
Patent number
US07741320B2

Reaction notes

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