3,4,5-Trimethoxybenzoic Acid → HCID 1359240, compound

HRID 993003Notes

Reaction equation

HRID 993003 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O.[NH2:16][C:17]1[S:18][CH:19]=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:21]=1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:15][O:14][C:10]1[CH:9]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:11]=1[O:12][CH3:13])[C:6]([NH:16][C:17]1[S:18][CH:19]=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:21]=1)=[O:8]

Participants

5

Reactant 2

HCID 83573,4,5-Trimethoxybenzoic AcidHCID 73216Ethyl 2-aminothiazole-4-carboxylate

Product 1

HCID 1359240HCID 1359240, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

3,4,5-Trimethoxybenzoic acid (3.69 g), ethyl 2-aminothiazole-4-carboxylate (3.0 g) and 4-(dimethylamino)-pyridine (702 mg) were dissolved in dichloromethane (80 mL), and to the solution was added 1-ethyl-3-(3-dimethyl-aminopropyl)carbodiimide hydrochloride (water-soluble carbodiimide hydrochloride) (3.34 g). The mixture was stirred overnight at room temperature and then concentrated under reduced pressure, and the residue was dissolved in ethyl acetate. The solution was successively washed with 2 M hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine, and dried over anhydrous sodium sulfate. After concentrating the organic layer under reduced pressure, the residue was purified by column chromatography on silica gel (chloroform:methanol=30:1) to obtain the title compound.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe solution was successively washed with 2 M hydrochloric acid
  4. dry with materiala saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine, and dried over anhydrous sodium sulfate
  5. concentrationAfter concentrating the organic layer under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-5c47c755df3947c6bf4ceef8f2bf1743
Source dataset
uspto-grants-2002_10
Patent number
US06472386B1

Reaction notes

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