Pyridine → N-(2-methyl-benzooxazol-6-yl)-4-propyl-benzenesulfonamide

HRID 970042Notes

Reaction equation

HRID 970042 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)[CH2:2][CH3:3].N1C=CC=CC=1.[NH2:20][C:21]1[CH:30]=[CH:29][C:24]2[N:25]=[C:26]([CH3:28])[O:27][C:23]=2[CH:22]=1.C([O-])(O)=O.[Na+]>ClCCl>[CH3:28][C:26]1[O:27][C:23]2[CH:22]=[C:21]([NH:20][S:10]([C:7]3[CH:8]=[CH:9][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=3)(=[O:12])=[O:11])[CH:30]=[CH:29][C:24]=2[N:25]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 5905392-Methyl-1,3-benzoxazol-6-amineHCID 27372224-N-Propylbenzenesulphonyl chloride

Product 1

HCID 59018250N-(2-methyl-benzooxazol-6-yl)-4-propyl-benzenesulfonamideYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4n-propylbenzenesulphonyl chloride (163 mg, 0.744 mmol) in dichloromethane (3 mL) was added pyridine (140 μL, 1.72 mmol) and the mixture was stirred under N2 for 5 min, after which time 6-amino-2-methylbenzoxazole (105 mg, 0.709 mmol) was added. The resulting mixture was stirred for 1 h at room temperature, then saturated NaHCO3 solution was added (8 mL) and the mixture was extracted into ethyl acetate (15 mL). The organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to give a residue that was purified using flash chromatography to afford a pale pink solid (164 mg, 70%), single spot at Rf 0.49 (60:40 hexane:ethyl acetate). mp 101.7-102.3° C., HPLC purity 99% (tR 2.02 min in 10% water-acetonitrile). 1H NMR (CDCl3): δ 7.61 (2H, m), 7.43 (1H, d, J=8.4 Hz), 7.37 (1H, d, J=1.8 Hz), 7.19 (2H, m), 6.83 (2H, m), 2.57 (5H, m), 1.58 (2H, sextet, J=7.3 Hz), 0.88 (3H, t, J=7.3 Hz). LCMS: 329.21 (M−). FAB-MS (MH+, C17H18N2O3S): calcd 331.1116, found 331.1107.

Workup

  1. stirringThe resulting mixture was stirred for 1 h at room temperature
  2. extractionthe mixture was extracted into ethyl acetate (15 mL)
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a residue that
  8. customwas purified

Sources & evidence

ORD record
ord-5d2ada7cf9114165ab07006bc72b0044
Source dataset
uspto-grants-2007_12
Patent number
US07309715B2

Reaction notes

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