Thionyl Chloride → HCID 12041317, compound

HRID 1268112Notes

Reaction equation

HRID 1268112 reaction equation
[N+:1]([C:4]1[CH:20]=[CH:19][C:7]([CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=2)[C:13]([OH:15])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)(Cl)=O.[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[S:32]([NH2:35])(=[O:34])=[O:33]>C1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=2)[C:13]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[S:32](=[O:34])(=[O:33])[NH2:35])=[O:15])=[CH:19][CH:20]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 728942-AminobenzenesulfonamideHCID 8706988HCID 8706988, compound

Product 1

HCID 12041317HCID 12041317, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A benzene (20 ml) solution containing 1.40 (5.1 mmol) of 3-(4-nitrobenzyloxy)benzoic acid and 2 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 (20 ml), this solution was added dropwise under ice-cooling to a pyridine (30 ml) solution containing 0.97 g (5.6 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 1.9 g (yield: 87.0%) 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 (20 ml)
  5. additionthis solution was added dropwise under ice-
  6. temperaturecooling to a pyridine (30 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-0d4a9a5ea1a8461ab75ada2082f92879
Source dataset
uspto-grants-2003_04
Patent number
US06555584B1

Reaction notes

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