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

HRID 1621070Notes

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

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

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

Sources & evidence

ORD record: ord-56c0ef1faf384b778322ad469cc4549f
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772528B2

Reaction notes

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