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

HRID 2196604Notes

Reaction equation

HRID 2196604 reaction equation
[CH3:1][N:2]1[CH:6]=[N:5][N:4]=[C:3]1[SH:7].CC(C)([O-])C.[K+].Cl[C:15]1[N:20]=[C:19]([C:21]([NH:23][C:24]2[S:28][N:27]=[C:26]([CH3:29])[N:25]=2)=[O:22])[C:18]([S:30][C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)=[CH:17][CH:16]=1.Cl>O.C(Cl)(Cl)Cl.CC(N(C)C)=O>[OH:37][C:34]1[CH:35]=[CH:36][C:31]([S:30][C:18]2[C:19]([C:21]([NH:23][C:24]3[S:28][N:27]=[C:26]([CH3:29])[N:25]=3)=[O:22])=[N:20][C:15]([S:7][C:3]3[N:2]([CH3:1])[CH:6]=[N:5][N:4]=3)=[CH:16][CH:17]=2)=[CH:32][CH:33]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 866196096-chloro-3-[(4-hydroxyphenyl)thio]-N-(3-methyl-1,2,4-thiadiazol-5-yl)pyridine-2-carboxamideHCID 178481306HCID 178481306, compound

Product 1

HCID 597062523-[(4-hydroxyphenyl)thio]-N-(3-methyl-1,2,4-thiadiazol-5-yl)-6-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]pyridine-2-carboxamideYield 63.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
160 °C

Procedure

20 g of 4-methyl-4H-1,2,4-triazole-3-thiol and 19 g of potassium t-butoxide were added to a dimethylacetamide (130 ml) solution of 13 g of 6-chloro-3-[(4-hydroxyphenyl)thio]-N-(3-methyl-1,2,4-thiadiazol-5-yl)pyridine-2-carboxamide, and stirred under heat at 160° C. for 8 hours. At room temperature, chloroform and water were added to it, and its pH was controlled to 3 with aqueous 1 N hydrochloric acid solution added thereto. This was extracted with chloroform, and the organic layer was washed with saturated saline water, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol) to obtain 10.0 g of the entitled compound as a yellow solid.

Workup

  1. additionadded
  2. extractionThis was extracted with chloroform
  3. washthe organic layer was washed with saturated saline water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated away under reduced pressure
  6. customthe residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol)

Sources & evidence

ORD record
ord-3b4e3bc0593b4f3c889d066f101fb31e
Source dataset
uspto-grants-2012_12
Patent number
US08338460B2

Reaction notes

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