Citric Acid → HCID 178487744, compound

HRID 1443452Notes

Reaction equation

HRID 1443452 reaction equation
[C:1]([C:4]1[C:9]([NH:10][C:11]([C:13]2[S:14][CH:15]=[C:16]([CH:18]([CH3:20])[CH3:19])[N:17]=2)=O)=[C:8]([CH3:21])[C:7]([O:22][CH3:23])=[CH:6][CH:5]=1)(=[O:3])[NH2:2].C(=O)([O-])[O-].[Na+].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CCO.O>[CH:18]([C:16]1[N:17]=[C:13]([C:11]2[N:2]=[C:1]([OH:3])[C:4]3[C:9](=[C:8]([CH3:21])[C:7]([O:22][CH3:23])=[CH:6][CH:5]=3)[N:10]=2)[S:14][CH:15]=1)([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 311Citric AcidHCID 10340Sodium CarbonateHCID 591654334-Isopropylthiazole-2-carboxylic acid (6-carbamoyl-3-methoxy-2-methyl-phenyl)-amide

Product 1

HCID 178487744HCID 178487744, compoundYield 68.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The above amide (79) (3.0 g, 9 mmol) was refluxed for three hours in a mixture of sodium carbonate (2.4 g, 22.5 mmol) in EtOH (70 ml) and water (70 ml). The mixture was acidified with 5% citric acid and extracted three times with a mixture of ethyl acetate-THF (4:1). The organic phase was dried with sodium sulfate and evaporated under reduced pressure. The product was purified by column chromatography on silica gel eluted with DCM containing 3% MeOH which gave the title compound (1.95 g).

Workup

  1. extractionextracted three times
  2. additionwith a mixture of ethyl acetate-THF (4:1)
  3. dry with materialThe organic phase was dried with sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe product was purified by column chromatography on silica gel
  6. washeluted with DCM containing 3% MeOH which

Sources & evidence

ORD record
ord-8b5204e5c4564f5ba8ffee7bc13a364a
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

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