Potassium Carbonate → HCID 18707155, compound

HRID 1421968Notes

Reaction equation

HRID 1421968 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]([O:27][CH3:28])=[O:26])[CH:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:36][C:37]([O:39][CH3:40])=[O:38]>CN(C)C=O>[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][CH2:36][C:37]([O:39][CH3:40])=[O:38])=[C:20]([C:25]([O:27][CH3:28])=[O:26])[CH:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 18707277HCID 18707277, compound

Product 1

HCID 18707155HCID 18707155, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 10 ml of dimethylformamide were suspended 1 g of 2-(3,4-diethoxyphenyl)-4-(4-hydroxy-3-methoxycarbonylphenyl)thiazole and 0.35 g of potassium carbonate. The suspension was stirred at room temperature for 30 minutes. Thereto was added 0.46 g of methyl bromoacetate. The mixture was stirred at the same temperature for 4 hours. The solvent was removed by distillation. The residue was extracted with 40 ml of dichloromethane. The extract was washed with 10 ml of water and 10 ml of a saturated aqueous sodium chloride solution, dried over magnesium sulfate, and subjected to distillation to remove the solvent. The residue was recrystallized from diisopropyl ether to obtain 1.1 g of 2-(3,4-diethoxyphenyl)-4-(4-methoxycarbonylmethoxy-3-methoxycarbonylphenyl)thiazole.

Workup

  1. stirringThe mixture was stirred at the same temperature for 4 hours
  2. customThe solvent was removed by distillation
  3. extractionThe residue was extracted with 40 ml of dichloromethane
  4. washThe extract was washed with 10 ml of water and 10 ml of a saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. distillationsubjected to distillation
  7. customto remove the solvent
  8. customThe residue was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-81daedd3e8d14df2b4be1374783399b3
Source dataset
uspto-grants-2000_06
Patent number
US06080764

Reaction notes

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