Triethylamine → 4,5-bis(4-methoxyphenyl)-2-(N,N-dimethylcarbamoyl)thiazole

HRID 1587404Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([C:22]([O:24]CC)=O)[S:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.Cl.[CH3:28][NH:29][CH3:30].C(N(CC)CC)C>C(O)C.C(OCC)(=O)C.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([C:22](=[O:24])[N:29]([CH3:30])[CH3:28])[S:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4,5-bis(4-methoxyphenyl)-2-ethoxycarbonylthiazole (1.50 g), dimethylamine hydrochloride (6.62 g) and triethylamine (11.32 ml) in ethanol (15 ml) was heated at 100° C. for 85 hours in a sealed tube. After allowing to cool to ambient temperature, the mixture was dissolved in ethyl acetate and water. The separated organic layer was washed with water and brine, dried over magnesium sulfate and treated with activated charcoal. After filtration, the filtrate was evaporated in vacuo. The residue was subjected to column chromatography on silica gel (75 g) and eluted with chloroform. The fractions containing the object compound were combined and evaporated in vacuo, to give a oily compound of 4,5-bis(4-methoxyphenyl)-2-(N,N-dimethylcarbamoyl)thiazole (0.36 g).

Workup

temperatureto cool to ambient temperature
washThe separated organic layer was washed with water and brine
dry with materialdried over magnesium sulfate
additiontreated with activated charcoal
filtrationAfter filtration
customthe filtrate was evaporated in vacuo
washeluted with chloroform
additionThe fractions containing the object compound
customevaporated in vacuo

Sources & evidence

ORD record: ord-d6e16e8a19354fecaace097e91374bd9
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05217971

Reaction notes

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