2-Aminothiazole → HCID 17587495, compound

HRID 1798962Notes

Reaction equation

HRID 1798962 reaction equation
[Cl:1][C:2]1[C:3]([C:9]([OH:11])=O)=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.[CH:12]1[N:16]=[C:15]([NH2:17])[S:14][CH:13]=1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:3]([C:9]([NH:17][C:15]2[S:14][CH:13]=[CH:12][N:16]=2)=[O:11])=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 15553ClopyralidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 17587495HCID 17587495, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution (400 ml) of 14.1 g (73.0 mmol) of 3,6-dichloro-2-pyridinecarboxylic acid in chloroform were successively added 9.00 g (89.9 mmol) of aminothiazole, 12.1 g (89.7 mmol) of N-hydroxybenzotriazole hydrate and 19.0 g (99.2 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride followed by stirring at room temperature for 24 hours. After the reaction solution was concentrated, ethyl acetate was added to the residue followed by washing with 0.2N aqueous solution of hydrochloric acid, water and saturated aqueous solution of sodium hydrogen carbonate. After drying and concentrating, the resulting residue was crystallized from a mixed solvent of hexane and ethyl acetate (5:1) to give 12.8 g (yield: 64%) of 3,6-dichloro-N-(thiazole-2-yl)-2-pyridine carboxamide as a white solid.

Workup

  1. concentrationAfter the reaction solution was concentrated
  2. additionethyl acetate was added to the residue
  3. washby washing with 0.2N aqueous solution of hydrochloric acid, water and saturated aqueous solution of sodium hydrogen carbonate
  4. customAfter drying
  5. concentrationconcentrating
  6. customthe resulting residue was crystallized from a mixed solvent of hexane and ethyl acetate (5:1)

Sources & evidence

ORD record
ord-944459e6617545e1a6599a61fe1d4c65
Source dataset
uspto-grants-2013_01
Patent number
US08344003B2

Reaction notes

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