Sodium Hydroxide → HCID 58778853, compound

HRID 1372568Notes

Reaction equation

HRID 1372568 reaction equation
[Cl: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]=[C:16]([CH2:18][C:19]([O:21]C)=[O:20])[CH:15]=[CH:14][C:12]=2[N:13]=1.[OH-].[Na+]>C1COCC1>[Cl: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]=[C:16]([CH2:18][C:19]([OH:21])=[O:20])[CH:15]=[CH:14][C:12]=2[N:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58779049Methyl 2-(2-chlorophenylamino)-6-benzoxazolylacetate

Product 1

HCID 58778853HCID 58778853, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In THF (200 ml) was dissolved methyl 2-(2-chlorophenylamino)-6-benzoxazolylacetate (3.35 g, 10.6 mmol). After addition of 0.25N NaOH (200 ml), the mixture was stirred at room temperature for 16 hours. The reaction mixture was distilled under reduced pressure to remove the solvent. The residue was acidified with 1N HCl, followed by extraction 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 (2.94 g, 92%) was obtained as a pale brown solid.

Workup

  1. distillationThe reaction mixture was distilled under reduced pressure
  2. customto remove the solvent
  3. extractionfollowed by extraction with a chloroform/methanol (10/1) mixture
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent, whereby the title compound (2.94 g, 92%)
  8. customwas obtained as a pale brown solid

Sources & evidence

ORD record
ord-371c2bf909ff41598167474918e261e3
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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