Sodium Hydroxide → HCID 58778391, compound

HRID 1372595Notes

Reaction equation

HRID 1372595 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]([O:21]C)=[O:20])=[CH:14][C:12]=2[N:13]=1.[OH-].[Na+]>C1COCC1>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:21])=[O:20])=[CH:14][C:12]=2[N:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58778342HCID 58778342, compound

Product 1

HCID 58778391HCID 58778391, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(2-methylphenylamino)-5-benzoxazolylacetate (2.32 g, 7.86 mmol) was dissolved in THF (40 ml). After addition of 0.25N NaOH (40 ml) under stirring at room temperature, the mixture was stirred for 15 hours. The residue, which had been obtained by distilling the reaction mixture under reduced pressure to remove the solvent, was acidified with 1N HCl. The crystals thus obtained were collected by filtration under reduced pressure, washed with water, dried under reduced pressure, whereby the title compound (894 mg) was obtained as a pale black crystalline powder. The water layer was extracted with a chloroform/methanol (10/1) mixture. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent, whereby the title compound (1.03 g) was obtained as a colorless solid (total yield: 88%).

Workup

  1. stirringthe mixture was stirred for 15 hours
  2. customThe residue, which had been obtained
  3. distillationby distilling the reaction mixture under reduced pressure
  4. customto remove the solvent
  5. customThe crystals thus obtained
  6. filtrationwere collected by filtration under reduced pressure
  7. washwashed with water
  8. dry with materialdried under reduced pressure, whereby the title compound (894 mg)
  9. customwas obtained as a pale black crystalline powder
  10. extractionThe water layer was extracted with a chloroform/methanol (10/1) mixture
  11. washThe extract was washed with saturated brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. distillationdistilled under reduced pressure
  14. customto remove the solvent, whereby the title compound (1.03 g)
  15. customwas obtained as a colorless solid (total yield: 88%)

Sources & evidence

ORD record
ord-3b95ca63cf1e484780ca17acdc4ae6a1
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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