2-Chloronicotinic acid → HCID 178512705, compound

HRID 1904005Notes

Reaction equation

HRID 1904005 reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])[N:9]=1)[C:2]([NH2:4])=[NH:3].Cl[C:16]1[C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=[CH:18][N:17]=1>O>[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:16]2[C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=[CH:18][N:17]=2)[N:9]=1)[C:2]([NH2:4])=[NH:3]

Participants

4

Reactant 2

HCID 762582-Chloronicotinic acidHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Product 1

HCID 178512705HCID 178512705, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An intimate mixture of 2-(2-guanidino-4-thiazolylmethylthio)ethylamine (2.31 g; 0.010 moles) and 2-chloropyridine-3-carboxylic acid (1.58 g; 0.010 moles) was heated to 140° for 3 hours. After cooling the mixture, it was dissolved in hot water and the solution was filtered hot. On leaving the filtrate to stand, a solid mass deposited. This was filtered off and recrystallised from water to give 2-[2-(2-guanidino-4-thiazolylmethylthio)ethyl]aminopyridine-3-carboxylic acid (0.60 g) as a beige-coloured solid m.p. 141°-5°.

Workup

  1. temperaturewas heated to 140° for 3 hours
  2. temperatureAfter cooling the mixture, it
  3. filtrationthe solution was filtered hot
  4. customOn leaving the filtrate
  5. filtrationThis was filtered off
  6. customrecrystallised from water

Sources & evidence

ORD record
ord-e468cde5288f49e1b6cb53a18d43ee0a
Source dataset
uspto-grants-1984_03
Patent number
US04439437

Reaction notes

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