Pyridine → N-(2-methyl-benzooxazol-5-yl)-4-propyl-benzenesulfonamide

HRID 970044Notes

Reaction equation

HRID 970044 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:22]=[CH:23][C:24]2[O:28][C:27]([CH3:29])=[N:26][C:25]=2[CH:30]=1.C([O-])(O)=O.[Na+]>ClCCl>[CH3:29][C:27]1[O:28][C:24]2[CH:23]=[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][C:25]=2[N:26]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 7379202-Methyl-1,3-benzoxazol-5-amineHCID 27372224-N-Propylbenzenesulphonyl chloride

Product 1

HCID 11724187N-(2-methyl-benzooxazol-5-yl)-4-propyl-benzenesulfonamideYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4n-propylbenzenesulphonyl chloride (93 mg, 0.43 mmol) in dichloromethane (2 mL) was added pyridine (80 μL, 1.0 mmol) and the mixture was stirred under N2 for 5 min, after which time 5-amino-2-methylbenzoxazole (60 mg, 0.40 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 oil (112 mg, 85%), single spot at Rf 0.53 (1:1 hexane:ethyl acetate). HPLC purity 99+% (tR 2.38 min in 10% water-acetonitrile) 1H NMR (CDCl3): δ 7.64 (2H, dt, J=8.1, 1.8 Hz), 7.31 (2H, m), 7.18 (2H, d, J=8.4 Hz), 7.06 (1H, dd, J=8.6, 2.4 Hz), 2.59 (5H, m), 1.58 (2H, sextet, J=7.3 Hz), 0.89 (3H, t, J=7.3 Hz). LCMS: 329.15 (M−). FAB-MS (MH+, C17H18N2O3S): calcd 331.1116, found 331.1118.

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-3df574cc829340469b0b4aefc808826a
Source dataset
uspto-grants-2007_12
Patent number
US07309715B2

Reaction notes

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