Acetic Anhydride → HCID 18707199, compound

HRID 1489262Notes

Reaction equation

HRID 1489262 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([C:25]([OH:27])=[O:26])[CH:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].[C:28](OC(=O)C)(=[O:30])[CH3:29]>>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][C:28](=[O:30])[CH3:29])=[C:20]([C:25]([OH:27])=[O:26])[CH:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 18707273HCID 18707273, compound

Product 1

HCID 18707199HCID 18707199, compound

Procedure

A solution of 1 g of 2-(3,4-diethoxyphenyl)-4-(3-carboxy-4-hydroxyphenyl)thiazole in 5 ml of acetic anhydride was stirred at 100° C. for 4 hours with heating. The solvent was distilled off. The residue was dissolved in 50 ml of ethyl acetate. To the solution was added 10 ml of a saturated sodium hydrogencarbonate solution, and phase separation was conducted. The ethyl acetate layer was made acidic with 10% hydrochloric acid, washed with 10 ml of a saturated aqueous sodium chloride solution, dried and subjected to distillation to remove the solvent. The residue was recrystallized from ethyl acetate to obtain 145 mg of 2-(3,4-diethoxyphenyl)-4-(3-carboxy-4-acetyloxyphenyl)thiazole.

Workup

  1. temperaturewith heating
  2. distillationThe solvent was distilled off
  3. dissolutionThe residue was dissolved in 50 ml of ethyl acetate
  4. additionTo the solution was added
  5. custom10 ml of a saturated sodium hydrogencarbonate solution, and phase separation
  6. washwashed with 10 ml of a saturated aqueous sodium chloride solution
  7. customdried
  8. distillationsubjected to distillation
  9. customto remove the solvent
  10. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9fcd4dec1947481eb4ffc2449c9c9d9c
Source dataset
uspto-grants-1997_10
Patent number
US05677319

Reaction notes

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