Hydrochloric Acid → HCID 19872511, compound

HRID 477888Notes

Reaction equation

HRID 477888 reaction equation
C([O:4][C:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:19](=[O:20])[N:18]([CH3:21])[C:17]3[CH:22]=[C:23]([O:26][CH:27]([CH3:29])[CH3:28])[CH:24]=[CH:25][C:16]=3[S:15]2(=[O:31])=[O:30])=[CH:10][CH:9]=1)=[O:6])(C)C.O.Cl>O1CCOCC1>[C:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:19](=[O:20])[N:18]([CH3:21])[C:17]3[CH:22]=[C:23]([O:26][CH:27]([CH3:28])[CH3:29])[CH:24]=[CH:25][C:16]=3[S:15]2(=[O:31])=[O:30])=[CH:10][CH:9]=1)([OH:6])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 19872501HCID 19872501, compound

Product 1

HCID 19872511HCID 19872511, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-(4-isopropoxycarbonylmethylphenyl)-6-isopropoxy-4-methyl-2H-1,2,4-benzothiadiazine-3(4H)-one 1,1-dioxide (95 mg) in a mixture of 1,4-dioxane (6 ml), water (2 ml) and conc. hydrochloric acid (1 ml) was refluxed for two hours. After the mixture was concentrated in vacuo, the residue was extracted two times with ethyl acetate. The combined organic layers were washed with water and brine, dried over MgSO4. After the solvent was evaporated under reduced pressure, the crystalline residue was recrystallized from ethanol to yield 2-(4-carboxymethylphenyl)-6-isopropoxy-4-methyl-2H-1,2,4-benzothiadiazine-3(4H)-one 1,1-dioxide (61 mg) as pale yellow crystals.

Workup

  1. temperaturewas refluxed for two hours
  2. concentrationAfter the mixture was concentrated in vacuo
  3. extractionthe residue was extracted two times with ethyl acetate
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over MgSO4
  6. customAfter the solvent was evaporated under reduced pressure
  7. customthe crystalline residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-304a882cb7b643d8988838f0be3e3cb7
Source dataset
uspto-grants-1989_12
Patent number
US04889851

Reaction notes

Loading…