Hydrochloric Acid → HCID 86743629, compound

HRID 477891Notes

Reaction equation

HRID 477891 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=O)[N:12]([CH3:15])[C:11]3[CH:16]=[C:17]([O:20][CH2:21][CH2:22][N:23]4C(=O)C5=CC=CC=C5C4=O)[CH:18]=[CH:19][C:10]=3[S:9]2(=O)=O)=[CH:4][CH:3]=1.O.NN.Cl>CO>[NH2:23][CH2:22][CH2:21][O:20][C:17]1[CH:18]=[CH:19][C:10]2[S:9][N:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH2:13][N:12]([CH3:15])[C:11]=2[CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 19872513HCID 19872513, compound

Product 1

HCID 86743629HCID 86743629, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(4-chlorophenyl)-4-methyl-6-(2-phthalimidoethoxy)-2H-1,2,4-benzothiadiazine-3(4H)-one 1,1-dioxide (0.153 g) in methanol (1.5 ml) was added hydrazine monohydrate (30 mg). After the mixture was refluxed for one hour, the reaction mixture was treated with conc. HCl and further refluxed for 30 minutes. The precipitate was removed by filtration and the filtrate was washed two times with ether. The aqueous layer was treated with aqueous 1N NaOH solution and extracted with ethyl acetate. The extract was washed with brine and dried over MgSO4. After the solvent was evaporated under reduced pressure, the residue was triturated with IPE. The colorless crystals were collected by filtration and recrystallized from ethanol to give 6-(2-aminoethoxy)-2-(4-chlorophenyl)-4-methyl-2H-1,2,4-benzothiadiazine-(3-(4H)-one 1,1-dioxide (30 mg) as colorless prisms.

Workup

  1. temperatureAfter the mixture was refluxed for one hour
  2. temperaturefurther refluxed for 30 minutes
  3. customThe precipitate was removed by filtration
  4. washthe filtrate was washed two times with ether
  5. additionThe aqueous layer was treated with aqueous 1N NaOH solution
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with brine
  8. dry with materialdried over MgSO4
  9. customAfter the solvent was evaporated under reduced pressure
  10. customthe residue was triturated with IPE
  11. filtrationThe colorless crystals were collected by filtration
  12. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-17ac839be5954a82ac2e39afef375f95
Source dataset
uspto-grants-1989_12
Patent number
US04889851

Reaction notes

Loading…