Sodium Hydroxide → HCID 20212022, compound

HRID 1904004Notes

Reaction equation

HRID 1904004 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][S:7][CH2:8][CH2:9][NH2:10].[O-]CC.[Na+].Cl[C:16]1[C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=[CH:18][N:17]=1.[OH-].[Na+]>O>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][S:7][CH2:8][CH2:9][NH:10][C:16]1[C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=[CH:18][N:17]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 762582-Chloronicotinic acidHCID 2723922Sodium ethoxideHCID 129234032-[(Thiazol-2-yl)methylthio]ethylamine

Product 1

HCID 20212022HCID 20212022, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An intimate mixture of 2-(2-thiazolylmethylthio)ethylamine [prepared from 6.73 g; 0.020 moles of the dihydrobromide salt and sodium ethoxide (from 0.92 g; 0.040 g. atom of sodium in ethanol)] and 2-chloropyridine 3-carboxylic acid (3.15 g; 0.020 moles) was heated to 150° for 3 hours. The resulting brown residue was cooled, dissolved in a little water, and basified to pH5 by dropwise addition of 2 N sodium hydroxide solution, to precipitate an oil. The latter was separated and dried, and chromatographed on a column of silica-gel using chloroform/ethyl acetate, (1:1). The crude product was then recrystallised from isopropanol to give 2-[2-(2-thiazolylmethylthio)ethyl]amino pyridine 3-carboxylic acid as a cream-coloured solid (0.36 g, m.p. 133°-4° (softening above 123°).

Workup

  1. temperaturewas heated to 150° for 3 hours
  2. temperatureThe resulting brown residue was cooled
  3. customto precipitate an oil
  4. customThe latter was separated
  5. customdried
  6. customchromatographed on a column of silica-gel
  7. customThe crude product was then recrystallised from isopropanol

Sources & evidence

ORD record
ord-1375cc984fab46479be46e1e5208a7e4
Source dataset
uspto-grants-1984_03
Patent number
US04439437

Reaction notes

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