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Thionyl Chloride → 3-(4-Methoxybenzyloxy)-N-(2-sulfamoylphenyl)benzamide

HRID 1268116
Notes
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Reaction equation

HRID 1268116 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([OH:14])=O)=[CH:5][CH:4]=1.S(Cl)(Cl)=O.[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31]([NH2:34])(=[O:33])=[O:32]>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[S:31](=[O:33])(=[O:32])[NH2:34])=[O:14])=[CH:18][CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 728942-AminobenzenesulfonamideHCID 176073513-(4-Methoxybenzyloxy)benzoic acid

Product 1

HCID 120413193-(4-Methoxybenzyloxy)-N-(2-sulfamoylphenyl)benzamideYield 31%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A benzene (30 ml) solution containing 4.00 g (15.5 mmol) of 3-(4-methoxybenzyloxy)benzoic acid and 3 ml of thionyl chloride was heated under reflux for 2 hours and then the solvent was evaporated under a reduced pressure. The resulting residue was dissolved in methylene chloride (30 ml), this solution was added dropwise under ice-cooling to a pyridine (50 ml) solution containing 2.93 g (17.0 mmol) of 2-aminobenzenesulfonamide, the mixture was stirred at room temperature for 18 hours and then methylene chloride was evaporated under a reduced pressure. The resulting residue was dissolved in ethyl acetate, washed with a 1 N hydrochloric acid aqueous solution, water and saturated brine in that order and dried over anhydrous sodium sulfate, and then the solvent was evaporated under a reduced pressure. The thus obtained residue was purified by a silica gel chromatography to obtain 1.5 g (yield: 31.0%) of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customthe solvent was evaporated under a reduced pressure
  4. dissolutionThe resulting residue was dissolved in methylene chloride (30 ml)
  5. additionthis solution was added dropwise under ice-
  6. temperaturecooling to a pyridine (50 ml) solution
  7. custommethylene chloride was evaporated under a reduced pressure
  8. dissolutionThe resulting residue was dissolved in ethyl acetate
  9. washwashed with a 1 N hydrochloric acid aqueous solution, water and saturated brine in that order
  10. dry with materialdried over anhydrous sodium sulfate
  11. customthe solvent was evaporated under a reduced pressure
  12. customThe thus obtained residue was purified by a silica gel chromatography

Sources & evidence

ORD record
ord-a8bd65a0433342d6b3a939c176ea6134
Source dataset
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06555584B1

Reaction notes

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