Thionyl Chloride → HCID 12041325, compound

HRID 1268126Notes

Reaction equation

HRID 1268126 reaction equation
[F:1][C:2]([F:21])([F:20])[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.[NH2:26][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>[F:20][C:2]([F:1])([F:21])[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:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[S:33](=[O:35])(=[O:34])[NH2:36])=[O:14])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 728942-AminobenzenesulfonamideHCID 18544144HCID 18544144, compound

Product 1

HCID 12041325HCID 12041325, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A benzene (30 ml) solution containing 4.00 g (14.1 mmol) of 3-(4-trifluoromethylbenzyloxy)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 2.66 g (15.4 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 washed with methanol to obtain 5.10 g (yield: 80.0%) 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. washwere washed with methanol

Sources & evidence

ORD record
ord-5ed3f3d0caca474ca34a6b298eeba582
Source dataset
uspto-grants-2003_04
Patent number
US06555584B1

Reaction notes

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