Sodium hydride → HCID 131715156, compound

HRID 979441Notes

Reaction equation

HRID 979441 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[C:12]([N+:21]([O-:23])=[O:22])=[CH:13][C:14]2[O:18][C:17](=[O:19])[NH:16][C:15]=2[CH:20]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:24]([C:29]1[CH:43]=[C:42]([C:44]([CH2:47][CH3:48])([CH3:46])[CH3:45])[CH:41]=[CH:40][C:30]=1[O:31][C:32](=[O:39])[CH:33](Cl)[CH2:34][CH2:35][CH2:36][CH3:37])([CH2:27][CH3:28])([CH3:26])[CH3:25]>>[C:24]([C:29]1[CH:43]=[C:42]([C:44]([CH2:47][CH3:48])([CH3:45])[CH3:46])[CH:41]=[CH:40][C:30]=1[O:31][C:32](=[O:39])[CH:33]([N:16]1[C:15]2[CH:20]=[C:11]([O:10][CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:12]([N+:21]([O-:23])=[O:22])=[CH:13][C:14]=2[O:18][C:17]1=[O:19])[CH2:34][CH2:35][CH2:36][CH3:37])([CH2:27][CH3:28])([CH3:25])[CH3:26]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 20200128HCID 20200128, compoundHCID 131715157HCID 131715157, compound

Product 1

HCID 131715156HCID 131715156, compoundYield 72.8%

Procedure

60% sodium hydride in oil dispersion (3 g, 0.075 mole) was added to the benzoxazolone ((d), 18.12 g, 0.063 mole) and α-(2,4-ditert.-pentylphenoxy)-hexanoylchloride (23.23 g, 0.063 mole) in dry refluxing toluene (400 ml) and the resulting solution was refluxed for further 2 hours. Water (100 ml) was added and azeotropically distilled. The organic solution was filtered and evaporated to dryness under vacuum. The oily residue was purified by column chromatography on silica gel using toluene as eluant. The obtained yellow oil was crystallized from methanol (150 ml) to give the acylated benzoxazolone ((e), 28.3 g, 72.5%) as white prisms. The product structure was confirmed by NMR and IR spectra.

Workup

  1. customin dry
  2. temperaturerefluxing toluene (400 ml)
  3. temperaturethe resulting solution was refluxed for further 2 hours
  4. additionWater (100 ml) was added
  5. distillationazeotropically distilled
  6. filtrationThe organic solution was filtered
  7. customevaporated to dryness under vacuum
  8. customThe oily residue was purified by column chromatography on silica gel
  9. customThe obtained yellow oil was crystallized from methanol (150 ml)

Sources & evidence

ORD record
ord-029d02c2ee8247c9bbd376b7d95cb146
Source dataset
uspto-grants-1987_05
Patent number
US04668610

Reaction notes

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