Thionyl Chloride → HCID 18544091, compound

HRID 1268129Notes

Reaction equation

HRID 1268129 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)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].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]>C1C=CC=CC=1>[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])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 728942-AminobenzenesulfonamideHCID 143687603-(Heptyloxy)benzoic acid

Product 1

HCID 18544091HCID 18544091, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A benzene (30 ml) solution containing 3 g (12.5 mmol) of 3-heptyloxybenzoic 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 2.50 g (14.5 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 acetonitrile to obtain 3.00 g (yield: 60.0%) of the title compound. NMR (DMS-d6) δ: 0.87 (3 H, t, J=7 Hz), 1.22-1.50 (8 H, m), 1.70-1.80 (2 H, M), 4.41 (2 H, t, J=7 Hz), 7.17-7.23 (1 H, m), 7.33 (1 H, ddd, J=8 Hz, 8 Hz, 2 Hz), 7.77 (2 H, s), 7.90 (1 H, dd, J=8 Hz, 2 Hz), 8.48 (1 H, d, J=8 Hz), 10.38 (1 H, s)

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 acetonitrile

Sources & evidence

ORD record
ord-41794fabb33b438f8ed219fbd073f905
Source dataset
uspto-grants-2003_04
Patent number
US06555584B1

Reaction notes

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