Thionyl Chloride → Acetonitrile

HRID 1268096Notes

Reaction equation

HRID 1268096 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29]([NH2:32])(=[O:31])=[O:30].C(=O)(O)[O-].[Na+]>O1CCOCC1.C1C=CC=CC=1>[C:23](#[N:22])[CH3:24].[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29](=[O:31])(=[O:30])[NH2:32])=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 24386Thionyl ChlorideHCID 728942-AminobenzenesulfonamideHCID 3092263-(Benzyloxy)benzoic acidHCID 516892Sodium Bicarbonate

Product 2

HCID 6342AcetonitrileYield 60%HCID 12041307HCID 12041307, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 312751,4-DioxaneSolvent

Procedure

A benzene (40 ml) solution containing 2 g (8.8 mol) of 3-benzyloxybenzoic acid and 8 ml of thionyl chloride was heated under reflux for 2 hours and then the solvent was evaporated. A dioxane (10 ml) solution of the resulting residue was added dropwise to a water-dioxane 1:1 (20 ml) solution containing 1.5 g (8.8 mol) of 2-aminobenzenesulfonamide and 1.62 g (19 mol) of sodium bicarbonate, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, dioxane was evaporated, the resulting residue was acidified by adding 1 N HCl under ice-cooling and extracted with ethyl acetate. The extract was washed with water and saturated brine and dried over anhydrous sodium sulfate, and then the solvent was evaporated under a reduced pressure. By recrystallizing the resulting residue from acetonitrile 2.0 g (yield: 60%) of the title compound was obtained.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customthe solvent was evaporated
  4. additionA dioxane (10 ml) solution of the resulting residue was added dropwise to a water-dioxane 1:1 (20 ml) solution
  5. customwas evaporated
  6. additionby adding 1 N HCl under ice-
  7. temperaturecooling
  8. extractionextracted with ethyl acetate
  9. washThe extract was washed with water and saturated brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. customthe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-940e4ec92e2e434392c2035a8e7e9b1d
Source dataset
uspto-grants-2003_04
Patent number
US06555584B1

Reaction notes

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