Pyridine → HCID 67332442, compound

HRID 1886917Notes

Reaction equation

HRID 1886917 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 67332442HCID 67332442, compoundYield 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-00fb8b170a7e46bdb9a74fda97950e62
Source dataset
uspto-grants-2013_08
Patent number
US08501713B2

Reaction notes

Loading…