2(3H)-Benzoxazolone → HCID 69480756, compound

HRID 856359Notes

Reaction equation

HRID 856359 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[O:10].[H-].[Na+].CS(O[CH2:18][CH2:19][C:20]1([CH3:31])[O:24][C:23]2=[N:25][C:26]([N+:28]([O-:30])=[O:29])=[CH:27][N:22]2[CH2:21]1)(=O)=O>CN(C=O)C>[CH3:31][C:20]1([CH2:19][CH2:18][N:3]2[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[O:1][C:2]2=[O:10])[O:24][C:23]2=[N:25][C:26]([N+:28]([O-:30])=[O:29])=[CH:27][N:22]2[CH2:21]1

Participants

5

Reactant 3

HCID 60432(3H)-BenzoxazoloneHCID 24758Sodium hydrideHCID 230810922-(2-Methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)ethyl methanesulfonate

Product 1

HCID 69480756HCID 69480756, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-benzoxazolinone (240 mg, 1.8 mmol), sodium hydride (67 mg, 1.95 mmol) and DMF (10 ml) was stirred at room temperature for 30 minutes. To the reaction mixture, 2-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-yl)ethyl methanesulfonate prepared in Example 42 (500 mg, 1.7 mmol) was added followed by stirring at 50-60° C. for 4 hours. The reaction mixture was allowed to return to room temperature and poured into ice-water. The precipitates were filtered off and recrystallized from ethanol to afford 3-[2-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)ethyl]-3H-benzoxazol-2-one (320 mg, yield 56%) as a light brown powder.

Workup

  1. stirringby stirring at 50-60° C. for 4 hours
  2. customto return to room temperature
  3. filtrationThe precipitates were filtered off
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-c6ea4866dae64990b428152d937d3208
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

Loading…