Salicyluric Acid → HCID 69599200, compound

HRID 1823956Notes

Reaction equation

HRID 1823956 reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1.[OH:17][C:18]1[CH:30]=[CH:29][CH:28]=[CH:27][C:19]=1[C:20](=[O:26])[NH:21][CH2:22][C:23]([OH:25])=O.[C:31]([O-])(=[O:33])[CH3:32].[Na+]>C(OC(=O)C)(=O)C>[C:31]([O:17][C:18]1[CH:30]=[CH:29][CH:28]=[CH:27][C:19]=1[C:20]1[O:26][C:23](=[O:25])/[C:22](=[CH:9]/[C:8]2[CH:11]=[CH:12][C:5]([O:4][C:3]3[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=3[Br:1])=[CH:6][CH:7]=2)/[N:21]=1)(=[O:33])[CH3:32]

Participants

5

Reactant 3

HCID 10253Salicyluric AcidHCID 517045Sodium AcetateHCID 131696974-(2-Bromophenoxy)benzaldehyde

Product 1

HCID 69599200HCID 69599200, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 4-(2-bromophenoxy)benzaldehyde (0.35 g, 1.26 mmol), 2-hydroxy hippuric acid (0.22 g, 1.14 mmol) and sodium acetate (0.12 g, 1.48 mmol) in acetic anhydride (1 mL) is heated to 60° C. on an orbital shaker for one hour and is then cooled to 0° C. The reaction mixture is then concentrated under reduced pressure at 45° C. to afford a crude yellow solid. This solid is washed with ice water (150 mL) and heptane (100 mL) and then dried under vacuum at 40° C. to provide 0.475 g of 2-{(4Z)-4-[4-(2-bromophenoxy)benzylidene]-5-oxo-4,5-dihydro-1,3-oxazol-2-yl}phenyl acetate.

Workup

  1. temperatureis then cooled to 0° C
  2. concentrationThe reaction mixture is then concentrated under reduced pressure at 45° C.
  3. customto afford a crude yellow solid
  4. washThis solid is washed with ice water (150 mL) and heptane (100 mL)
  5. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-bad85b259668464fba6b22ae6c3cb98f
Source dataset
uspto-grants-2006_05
Patent number
US07041690B2

Reaction notes

Loading…