Salicyluric Acid → HCID 69598887, compound

HRID 1823958Notes

Reaction equation

HRID 1823958 reaction equation
[Cl: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[Cl:1])=[CH:6][CH:7]=2)/[N:21]=1)(=[O:33])[CH3:32]

Participants

5

Reactant 3

HCID 10253Salicyluric AcidHCID 517045Sodium AcetateHCID 104897734-(2-chlorophenoxy)benzaldehyde

Product 1

HCID 69598887HCID 69598887, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 4-(2-chlorophenoxy)benzaldehyde-(0.193 g, 0.83 mmol, 2-hydroxy hippuric acid (0.147 g, 0.75 mmol) and sodium acetate (0.08 g, 0.975 mmol) in acetic anhydride (0.5 mL) is heated to 60° C. on an orbital shaker for one hour and is cooled to room temperature. The reaction mixture is concentrated under reduced pressure at 45° C. to provide an orange solid. The solid is washed with ice water (150 mL) and heptane (100 mL) and dried under vacuum at 40° C. to provide 0.32 g 2-{(4Z)-4-[4-(2-chlorophenoxy)benzylidene]-5-oxo-4,5-dihydro-1,3-oxazol-2-yl}phenyl acetate.

Workup

  1. temperatureis cooled to room temperature
  2. concentrationThe reaction mixture is concentrated under reduced pressure at 45° C.
  3. customto provide an orange solid
  4. washThe solid is washed with ice water (150 mL) and heptane (100 mL)
  5. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-77ed93c19a994bf1b49b79c21b5b2445
Source dataset
uspto-grants-2006_05
Patent number
US07041690B2

Reaction notes

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