HCID 23718671, compound → HCID 18707131, compound

HRID 1421973Notes

Reaction equation

HRID 1421973 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:19]=[C:20]([C:24]([NH:27]C(=O)C)=[CH:25][CH:26]=3)[C:21]([O-:23])=[O:22])[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].[K+]>O.[OH-].[K+]>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:26]=[CH:25][C:24]([NH2:27])=[C:20]([C:21]([OH:23])=[O:22])[CH:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

4

Reactant 1

HCID 23718671HCID 23718671, compound

Product 1

HCID 18707131HCID 18707131, compoundYield 20.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Procedure

A solution of 1 g of potassium 3-[2-(3,4-diethoxyphenyl)thiazole-4-yl]-6-acetylaminobenzoate in 50 ml of water and 10 ml of 30% potassium hydroxide was refluxed for 8 hours with heating. After the completion of a reaction, the solvent was removed by distillation. The residue was made weakly acidic with 10% hydrochloric acid and extracted with 80 ml of ethyl acetate. The extract was washed with 20 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 168 mg of 2-(3,4-diethoxyphenyl)-4-(3-carboxy-4-aminophenyl)thiazole.

Workup

  1. temperaturewith heating
  2. customAfter the completion of a reaction
  3. customthe solvent was removed by distillation
  4. extractionextracted with 80 ml of ethyl acetate
  5. washThe extract was washed with 20 ml of a saturated aqueous sodium chloride solution
  6. customdried
  7. distillationsubjected to distillation
  8. customto remove the solvent
  9. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a44671457a2c4b3fbf1ca31050dca2ff
Source dataset
uspto-grants-2000_06
Patent number
US06080764

Reaction notes

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