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

HRID 1268103

Reaction equation

HRID 1268103 reaction equation
[C:1]([C:5]1[CH:21]=[CH:20][C:8]([CH2:9][O:10][C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14](O)=[O:15])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)(Cl)=O.[NH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33]([NH2:36])(=[O:35])=[O:34]>C1C=CC=CC=1>[C:1]([C:5]1[CH:21]=[CH:20][C:8]([CH2:9][O:10][C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[S:33](=[O:35])(=[O:34])[NH2:36])=[O:15])=[CH:7][CH:6]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 728942-AminobenzenesulfonamideHCID 18544100Nurr1 agonist 7

Product 1

HCID 120413093-(4-t-Butylbenzyloxy)-N-(2-sulfamoylphenyl)benzamideYield 68.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A benzene (30 ml) solution containing 4.00 g (14.0 mmol) of 3-(4-t-butylbenzyloxy)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 2.42 g (14.0 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 crude crystals were recrystallized from an ether-hexane mixed solvent to obtain 4.2 g (yield: 68.0%) 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 crude crystals
  13. customwere recrystallized from an ether-hexane mixed solvent

Sources & evidence

ORD record
ord-0ab645b4f253488c8e8c06febf39e4b6
Source dataset
uspto-grants-2003_04
Patent number
US06555584B1

Linked notes

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