Ethanol → HCID 178507263, compound

HRID 496128Notes

Reaction equation

HRID 496128 reaction equation
[CH:1]1([C:7]2[NH:8][S:9](=[O:21])(=[O:20])[C:10]3[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:11]=3[N:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCO>[OH-].[Na+].[Pd]>[NH2:17][C:15]1[CH:14]=[CH:13][C:11]2[N:12]=[C:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[NH:8][S:9](=[O:21])(=[O:20])[C:10]=2[CH:16]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 178526448HCID 178526448, compound

Product 1

HCID 178507263HCID 178507263, compoundYield 40.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 14798Sodium HydroxideSolvent

Procedure

A stirred suspension of 3-cyclohexyl-7-nitro-1,2-dihydro-1,2,4-benzothiadiazine-1,1-dioxide (4.2 g; 14 mmol) and 10% Pd/C (400 mg) in abs. EtOH (100 ml) was hydrogenated at 1 bar. After consumption of the calculated amount of H2, the reaction mixture was filtered through celite. The celite was washed twice with DMF (75 ml) and the combined organic fractions were evaporated to dryness. The remanense was resuspended in EtOAc/i-PrOH and the precipitate formed, was isolated by filtration. The isolated solid was dissolved in 0.5 M NaOH (aq.) and reprecipitated with 4 M HCl (aq.). Filtration gave 1.6 g product.

Workup

  1. customAfter consumption of the calculated amount of H2
  2. filtrationthe reaction mixture was filtered through celite
  3. washThe celite was washed twice with DMF (75 ml)
  4. customthe combined organic fractions were evaporated to dryness
  5. customthe precipitate formed
  6. customwas isolated by filtration
  7. customreprecipitated with 4 M HCl (aq.)
  8. filtrationFiltration

Sources & evidence

ORD record
ord-81bc35b80618453eadc37b100b114442
Source dataset
uspto-grants-2005_09
Patent number
US06943159B1

Reaction notes

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