Nicotinic Acid → 6-Methoxy-2-(pyridin-2-yl)-1,3-benzothiazole

HRID 1287833Notes

Reaction equation

HRID 1287833 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[SH:10].C(O)(=O)[C:12]1[CH:17]=[CH:16][CH:15]=[N:14][CH:13]=1.[CH:20](Cl)(Cl)Cl>>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]2[N:1]=[C:20]([C:13]3[CH:12]=[CH:17][CH:16]=[CH:15][N:14]=3)[S:10][C:3]=2[CH:4]=1

Participants

4

Reactant 3

HCID 938Nicotinic AcidHCID 6212ChloroformHCID 2355092-Amino-5-methoxybenzene-1-thiol

Product 1

HCID 215066886-Methoxy-2-(pyridin-2-yl)-1,3-benzothiazole

Procedure

A mixture of 2-amino-5-methoxy-benzenethiol, 25 g (0.16 mole) and nicotinic acid, 24.6 g (0.2 mole) is dissolved in 250 cc of CHCl3 containing 160 g of PPE. The mixture is refluxed overnight. The mixture is concentrated to dryness and the residue poured on ice and the pH of the solution is adjusted to 10 using 50% NaOH solution. The precipitate is filtered, washed with water and dried to yield 34.5 g of the title compound.

Workup

  1. temperatureThe mixture is refluxed overnight
  2. concentrationThe mixture is concentrated to dryness
  3. additionthe residue poured on ice
  4. filtrationThe precipitate is filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-32028ef983e440e39019d94cfc9f3686
Source dataset
uspto-grants-1976_10
Patent number
US03985885

Reaction notes

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