Methanol → Methyl 2-(2-hydroxy-4,5-diMethoxybenzaMido)thiazole-4-carboxylate

HRID 78703

Reaction equation

HRID 78703 reaction equation
[N+](C1C=CC(O[C:11](=[O:23])[C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[CH:14][C:13]=2[OH:22])=CC=1)([O-])=O.[CH3:24][O:25][C:26]([C:28]1[N:29]=[C:30]([NH2:33])[S:31][CH:32]=1)=[O:27].CO>C1(C)C(C)=CC=CC=1>[CH3:24][O:25][C:26]([C:28]1[N:29]=[C:30]([NH:33][C:11](=[O:23])[C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[CH:14][C:13]=2[OH:22])[S:31][CH:32]=1)=[O:27]

Participants

5

Reactant 3

HCID 887MethanolHCID 840099Methyl 2-amino-1,3-thiazole-4-carboxylateHCID 66886647HCID 66886647, compound

Product 1

HCID 86711696Methyl 2-(2-hydroxy-4,5-diMethoxybenzaMido)thiazole-4-carboxylateYield 84.9%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
130 °C

Procedure

In 1 mL of xylene were suspended 200 mg of 2-hydroxy-4,5-dimethoxybenzoic acid 4-nitrophenyl ester and 119 mg of 2-amino-1,3-thiazole-4-carboxylic acid methyl ester in a stream of argon, which was then stirred at 130° C. for 12 hours. The reaction mixture was allowed to stand to cool, to which 1 mL of methanol was then added, followed by heating to reflux for one hour. The resultant reaction mixture was allowed to stand to cool, followed by collecting the precipitated crystal by filtration at 30° C. or lower before drying under reduced pressure to provide 180 mg of the title compound (5a) at a yield of 80%.

Workup

  1. additionwas then added
  2. temperatureby heating
  3. temperatureto reflux for one hour
  4. customThe resultant reaction mixture
  5. temperatureto cool
  6. customby collecting the precipitated crystal
  7. filtrationby filtration at 30° C.
  8. customlower before drying under reduced pressure

Sources & evidence

ORD record
ord-b659c56f7db54725a1a56263bd05b943
Source dataset
uspto-grants-2014_09
Patent number
US08841461B2

Linked notes

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