Hydrochloric Acid → HCID 87545492, compound

HRID 1818818Notes

Reaction equation

HRID 1818818 reaction equation
[O:1]=[S:2]1(=[O:31])[N:6]([CH2:7][CH2:8][C:9](=O)[CH2:10][N:11]([CH3:19])C(=O)OC(C)(C)C)[C:5]2[CH:21]=[CH:22][CH:23]=[CH:24][C:4]=2[N:3]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl.[NH2:33][OH:34].N1C=CC=CC=1.Cl>C(O)C.C(OCC)C.O1CCOCC1.CO.ClCCl>[O:1]=[S:2]1(=[O:31])[N:6]([CH2:7][CH2:8]/[C:9](=[N:33]/[OH:34])/[CH2:10][NH:11][CH3:19])[C:5]2[CH:21]=[CH:22][CH:23]=[CH:24][C:4]=2[N:3]1[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 86621290HCID 86621290, compound

Product 1

HCID 87545492HCID 87545492, compoundYield 69.4%

Reagents, catalysts & solvents 5

HCID 702EthanolSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-butyl [4-(2,2-dioxido-3-phenyl-2,1,3-benzothiadiazol-1(3H)-yl)-2-oxobutyl]methylcarbamate (50 mg, 0.112 mmol), hydroxylamine hydrochloride (50 mg, 0.720 mmol), and pyridine (1.5 mL) were stirred in ethyl alcohol (3 mL) in a sealed vial at 70° C., for 3 hr. The reaction was allowed to cool to room temperature and transferred to a separatory funnel with dichloromethane and washed with a saturation aqueous solution of sodium bicarbonate, brine, dried (MgSO4), filtered and the solvent removed, in vacuo, to give a clear oil. This material was adsorbed onto silica gel and purified via Isco chromatography (Redisep, silica, gradient 0-50% ethyl acetate in hexane to afford a white solid. This material was dissolved in diethyl ether and methanol and 4N HCl in dioxane was added a precipitate formed. The mixture was filtered to afford 0.028 g (62% Yield) of (2Z)-4-(2,2-dioxido-3-phenyl-2,1,3-benzothiadiazol-1(3H)-yl)-1-(methylamino)butan-2-one oxime as an off white solid.

Workup

  1. washwashed with a saturation aqueous solution of sodium bicarbonate, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent removed, in vacuo
  5. customto give a clear oil
  6. custompurified via Isco chromatography (Redisep, silica, gradient 0-50% ethyl acetate in hexane
  7. customto afford a white solid
  8. customformed
  9. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-9b5e5f3024d14d25a9ee905541a8ac38
Source dataset
uspto-grants-2009_10
Patent number
US07601722B2

Reaction notes

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