Nicotinic Acid → 5-Nitro-2-(pyridin-3-yl)-1,3-benzothiazole

HRID 1287830Notes

Reaction equation

HRID 1287830 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[SH:11].[C:12](O)(=O)[C:13]1[CH:18]=[CH:17][CH:16]=[N:15][CH:14]=1>C(Cl)(Cl)Cl>[N+:8]([C:6]1[CH:5]=[CH:4][C:3]2[S:11][C:12]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)=[N:1][C:2]=2[CH:7]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 938Nicotinic AcidHCID 63364002-Amino-4-nitrobenzenethiol

Product 1

HCID 127819025-Nitro-2-(pyridin-3-yl)-1,3-benzothiazoleYield 44%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Amino-4-nitrobenzenethiol,17 g, 0.10 mole, and nicotinic acid, 18.7 g, 0.15 mole, are heated 2 hours at reflux in 250 cc of CHCl3 containing 100 g of PPE. The solution is concentrated in vacuo, and the residue slurried in H2O. The pH is adjusted to 11 with 50% NaOH solution. The precipitate is filtered, washed with H2O and dried in vacuo to yield 11.2 g of tan solid m.p. 196°-198°, 44% of theory.

Workup

  1. concentrationThe solution is concentrated in vacuo
  2. filtrationThe precipitate is filtered
  3. washwashed with H2O
  4. customdried in vacuo

Sources & evidence

ORD record
ord-e00d44dc56264cfe8db09906761aa7fd
Source dataset
uspto-grants-1976_10
Patent number
US03985885

Reaction notes

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