Hydrochloric Acid → HCID 9907162, compound

HRID 1654958Notes

Reaction equation

HRID 1654958 reaction equation
[OH-].[Na+].BrBr.[O:5]1CCOCC1.[C:11]([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[CH2:19][CH:18]([CH2:23][NH:24][S:25]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)(=[O:27])=[O:26])[CH2:17]2)(=[O:13])C.S([O-])([O-])(=O)=S.[Na+].[Na+].Cl>O>[Cl:34][C:31]1[CH:30]=[CH:29][C:28]([S:25]([NH:24][CH2:23][CH:18]2[CH2:17][C:16]3[C:20](=[CH:21][CH:22]=[C:14]([C:11]([OH:13])=[O:5])[CH:15]=3)[CH2:19]2)(=[O:26])=[O:27])=[CH:33][CH:32]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24408BromineHCID 24477Sodium ThiosulfateHCID 312751,4-DioxaneHCID 18921491HCID 18921491, compound

Product 1

HCID 9907162HCID 9907162, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under ice-salt cooling, 4.90 g (122 mmol) of sodium hydroxide was dissolved in 50 ml of water, to which 1.6 ml (31.0 mmol) of bromine was added dropwise. This mixture was added to a solution of 100 ml of 90% dioxane containing 2.85 g (7.50 mmol) of 5-acetyl-2-[(4-chlorophenyl)sulfonylaminomethyl]indan under cooling in an ice-salt bath. Thereafter, stirring was conducted for 1 hour during which the temperature of the mixture was elevated to room temperature. The reaction solution was added with 10% sodium thiosulfate, and made acidic with 1N HCl, followed by extracting with ethyl acetate. The solvent was removed, and the residue was recrystallized from acetic acid to obtain 2.36 g of colorless crystals. Yield: 86%

Workup

  1. additionwas added dropwise
  2. temperatureunder cooling in an ice-salt bath
  3. customwas elevated to room temperature
  4. extractionby extracting with ethyl acetate
  5. customThe solvent was removed
  6. customthe residue was recrystallized from acetic acid

Sources & evidence

ORD record
ord-7e8db3b0d6ed44afb6d57399117d6d93
Source dataset
uspto-grants-1995_04
Patent number
US05409956

Reaction notes

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