Hydrochloric Acid → HCID 178464506, compound

HRID 496144Notes

Reaction equation

HRID 496144 reaction equation
[CH:1]1([C:7]2[NH:8][S:9](=[O:28])(=[O:27])[C:10]3[CH:16]=[C:15]([S:17](=[O:24])(=[O:23])[N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[CH:14]=[C:13]([CH:25]=O)[C:11]=3[N:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>CCO.[Pd]>[CH:1]1([C:7]2[NH:8][S:9](=[O:27])(=[O:28])[C:10]3[CH:16]=[C:15]([S:17](=[O:24])(=[O:23])[N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[CH:14]=[C:13]([CH3:25])[C:11]=3[N:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178464508HCID 178464508, compound

Product 1

HCID 178464506HCID 178464506, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-Cyclohexyl-7-(N,N-diethylsulphamoyl)-5-formyl-1,2-dihydro-1,2,4-benzothiadiazine-1,1-dioxide (0.20 g, 0.46 mmol) was dissolved in 99% EtOH (60 ml). One small drop of concentrated hydrochloric acid was added to ensure fully hydrogenation. The mixture was hydrogenated using Pd/C (10%, 10 mg) at 4 bar pressure for 24 h. The mixture was filtered through a pad of Celite M and evaporated to dryness. The residue was dissolved in EtOAc (50 ml) and washed with water (10 ml), dried (Na2SO4) and evaporated to dryness yielding 0.18 mg (95%) of 3-cyclohexyl-7-(N,N-diethylsulphamoyl)-5-methyl-1,2-dihydro-1,2,4-benzothiadiazine-1,1-dioxide as colorless powder. The product was further transformed by Method F. M.p. 206-208° C.

Workup

  1. customfor 24 h
  2. filtrationThe mixture was filtered through a pad of Celite M
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved in EtOAc (50 ml)
  5. washwashed with water (10 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-0676aeefae5048c5a7ee95ad1651d844
Source dataset
uspto-grants-2005_09
Patent number
US06943159B1

Reaction notes

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