Hydrochloric Acid → HCID 54175284, compound

HRID 477889Notes

Reaction equation

HRID 477889 reaction equation
[CH:1]1([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]3[S:17](=[O:19])(=[O:18])[N:16]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([O:28]CC5CCCCC5)=[O:27])=[CH:22][CH:21]=4)[C:15](=[O:36])[N:14]([CH3:37])[C:13]=3[CH:38]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.O>O1CCOCC1>[C:26]([C:23]1[CH:24]=[CH:25][C:20]([N:16]2[C:15](=[O:36])[N:14]([CH3:37])[C:13]3[CH:38]=[C:9]([O:8][CH2:7][CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)[CH:10]=[CH:11][C:12]=3[S:17]2(=[O:18])=[O:19])=[CH:21][CH:22]=1)([OH:28])=[O:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 54457963HCID 54457963, compound

Product 1

HCID 54175284HCID 54175284, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 6-cyclohexylmethoxy-2-(4-cyclohexylmethoxycarbonylphenyl)-4-methyl-2H-1,2,4-benzothiadiazine-3(4H)-one 1,1-dioxide (0.12 g) in a mixture of conc. hydrochloric acid (1 ml), water (2 ml) and 1,4-dioxane (8 ml) was refluxed overnight. The mixture was concentrated in vacuo. The residue was treated with a mixture of ethyl acetate and aqueous 1N sodium hydroxide solution. The precipitates were collected by filtration, washed with ethyl acetate and then dissolved in a mixture of ethyl acetate and aqueous 1N hydrochloric acid. The organic layer was washed with water, dried, and evaporated under reduced pressure. The residue was recrystallized from ethanol to give 2 -(4-carboxyphenyl)-6-cyclohexylmethoxy-4-methyl-2H-1,2,4-benzothiadiazine-3(4H)-one 1,1-dioxide as colorless crystals.

Workup

  1. temperaturewas refluxed overnight
  2. concentrationThe mixture was concentrated in vacuo
  3. additionThe residue was treated with a mixture of ethyl acetate and aqueous 1N sodium hydroxide solution
  4. filtrationThe precipitates were collected by filtration
  5. washwashed with ethyl acetate
  6. dissolutiondissolved in a mixture of ethyl acetate and aqueous 1N hydrochloric acid
  7. washThe organic layer was washed with water
  8. customdried
  9. customevaporated under reduced pressure
  10. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-68330b87e9fb4cbc9a58dbaaae179d46
Source dataset
uspto-grants-1989_12
Patent number
US04889851

Reaction notes

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