Tetrahydrofuran → 2-(2-(O-tolylamino)benzo[d]oxazol-6-yl)acetic acid

HRID 1372562Notes

Reaction equation

HRID 1372562 reaction equation
C1COCC1.[OH-].[Na+].[CH3:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]1[O:17][C:18]2[CH:24]=[C:23]([CH2:25][C:26]([O:28]C)=[O:27])[CH:22]=[CH:21][C:19]=2[N:20]=1>Cl>[CH3:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]1[O:17][C:18]2[CH:24]=[C:23]([CH2:25][C:26]([OH:28])=[O:27])[CH:22]=[CH:21][C:19]=2[N:20]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 53868986HCID 53868986, compound

Product 1

HCID 235083152-(2-(O-tolylamino)benzo[d]oxazol-6-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

THF (30 ml) and 0.25N NaOH (32 ml, 8.00 mmol) were added to methyl 2-(2-methylphenylamino)-6-benzoxazolylacetate (1.18 g, 3.98 mmol), followed by stirring at room temperature for 5 hours. The reaction mixture was poured in 1N HCl (50 ml), followed by extraction with a chloroform-methanol (5:1, 2×200 ml) mixture. The extract was dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent, whereby the title compound (867 mg, 77%) was obtained as a pale yellow amorphous substance.

Workup

  1. extractionfollowed by extraction with a chloroform-methanol (5:1, 2×200 ml) mixture
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. distillationdistilled under reduced pressure
  4. customto remove the solvent, whereby the title compound (867 mg, 77%)
  5. customwas obtained as a pale yellow amorphous substance

Sources & evidence

ORD record
ord-2e68ffd8ad614e81ab8754f7498b954c
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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