Clopyralid → 3,6-dichloro-N-(3-methyl-1,2,4-thiadiazol-5-yl)pyridine-2-carboxamide

HRID 2196602Notes

Reaction equation

HRID 2196602 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([CH3:7])[N:3]=1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[Cl:31][C:32]1[C:33]([C:39](O)=[O:40])=[N:34][C:35]([Cl:38])=[CH:36][CH:37]=1>C(Cl)(Cl)Cl>[Cl:31][C:32]1[C:33]([C:39]([NH:1][C:2]2[S:6][N:5]=[C:4]([CH3:7])[N:3]=2)=[O:40])=[N:34][C:35]([Cl:38])=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 15553ClopyralidHCID 3506395-Amino-3-methyl-1,2,4-thiadiazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 866196083,6-dichloro-N-(3-methyl-1,2,4-thiadiazol-5-yl)pyridine-2-carboxamideYield 75.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

12 g of 5-amino-3-methyl-1,2,4-thiadiazole, 21.1 g of N-hydroxybenzotriazole hydrate and 29.8 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added to a chloroform (500 ml) solution of 21 g of 3,6-dichloro-2-pyridinecarboxylic acid, and stirred at room temperature for 1 hour and then stirred overnight at 50° C. The reaction liquid was diluted with chloroform, then washed with aqueous 0.2 N hydrochloric acid solution, water and saturated saline water. After this was dried with anhydrous magnesium sulfate, the solvent was evaporated away under reduced pressure, and ethyl acetate was added to the resulting residue for crystallization to obtain 22.7 g of the entitled compound as a white solid.

Workup

  1. stirringstirred overnight at 50° C
  2. customThe reaction liquid
  3. washwashed with aqueous 0.2 N hydrochloric acid solution, water and saturated saline water
  4. dry with materialAfter this was dried with anhydrous magnesium sulfate
  5. customthe solvent was evaporated away under reduced pressure, and ethyl acetate
  6. additionwas added to the resulting residue for crystallization

Sources & evidence

ORD record
ord-ba8667fc15d84737a97990656eba2151
Source dataset
uspto-grants-2012_12
Patent number
US08338460B2

Reaction notes

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