Hydrochloric Acid → 6-chloro-3-[(4-hydroxyphenyl)thio]-N-(3-methyl-1,2,4-thiadiazol-5-yl)pyridine-2-carboxamide

HRID 2196603Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:16]1[C:17]([C:23]([NH:25][C:26]2[S:30][N:29]=[C:28]([CH3:31])[N:27]=2)=[O:24])=[N:18][C:19]([Cl:22])=[CH:20][CH:21]=1.Cl>O.C(Cl)(Cl)Cl.CN(C)C=O>[Cl:22][C:19]1[N:18]=[C:17]([C:23]([NH:25][C:26]2[S:30][N:29]=[C:28]([CH3:31])[N:27]=2)=[O:24])[C:16]([S:8][C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 50 °C

Procedure

12 g of 4-hydroxythiophenol and 16 g of potassium carbonate were added to a dimethylformamide (150 ml) solution of 15 g of 3,6-dichloro-N-(3-methyl-1,2,4-thiadiazol-5-yl)pyridine-2-carboxamide, and stirred at 50° C. for 1.5 hours. At room temperature, chloroform and water were added to it, and its pH was controlled to 3 with aqueous 2 N hydrochloric acid solution added thereto. This was extracted with chloroform, the organic layer was washed with saturated saline water, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, 300 ml of t-butyl methyl ether was added to the residue, and the resulting solid was taken out through filtration to obtain 14.1 g of the entitled compound as a yellow solid.

Workup

additionadded
extractionThis was extracted with chloroform
washthe organic layer was washed with saturated saline water
dry with materialdried with anhydrous magnesium sulfate
customThe solvent was evaporated away under reduced pressure, 300 ml of t-butyl methyl ether
additionwas added to the residue
filtrationthe resulting solid was taken out through filtration

Sources & evidence

ORD record: ord-9a0d1f3899ad495b9fbb8ede46593eef
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338460B2

Reaction notes

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