Pyridine → N-(2-Phenylbenzo[d]oxazol-5-yl)propane-1-sulfonamide

HRID 1896749Notes

Reaction equation

HRID 1896749 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[CH2:23]([S:26](Cl)(=[O:28])=[O:27])[CH2:24][CH3:25]>ClCCl>[C:1]1([C:7]2[O:8][C:9]3[CH:15]=[CH:14][C:13]([NH:16][S:26]([CH2:23][CH2:24][CH3:25])(=[O:28])=[O:27])=[CH:12][C:10]=3[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 662791-Propanesulfonyl chlorideHCID 7210592-Phenyl-1,3-benzoxazol-5-amine

Product 1

HCID 67332442N-(2-Phenylbenzo[d]oxazol-5-yl)propane-1-sulfonamideYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-phenylbenzo[d]oxazol-5-amine (100 mg, 0.48 mmol) in dichloromethane (2 mL) at room temperature was added pyridine (83 μL, 0.95 mmol) followed by propane-1-sulfonyl chloride (61 μL, 0.52 mmol). The resulting solution was then stirred at room temperature for 16 h. Dichloromethane was added and the organic layer was washed with saturated aqueous copper sulfate solution. The combined organic layers were dried over anhydrous MgSO4 and evaporated. The resulting insoluble solid was washed with saturated aqueous NaHCO3 to afford 37.2 mg (25%) of the title compound (LCMS RT=6.25 min, MH+ 317.0)

Workup

  1. washthe organic layer was washed with saturated aqueous copper sulfate solution
  2. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  3. customevaporated
  4. washThe resulting insoluble solid was washed with saturated aqueous NaHCO3

Sources & evidence

ORD record
ord-62d3ea13316847e8b5c03766ec62fdb4
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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