6-Chloro-2-benzothiazolamine → N-(6-Chloro-2-benzothiazolyl)-8-hydroxy-7-quinolinecarboxamide

HRID 382871

Reaction equation

HRID 382871 reaction equation
[OH:1][C:2]1[C:3]([C:12]([OH:14])=O)=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.P(Cl)(Cl)Cl.[NH2:19][C:20]1[S:21][C:22]2[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:23]=2[N:24]=1>O>[Cl:29][C:27]1[CH:26]=[CH:25][C:23]2[N:24]=[C:20]([NH:19][C:12]([C:3]3[C:2]([OH:1])=[C:11]4[C:6]([CH:7]=[CH:8][CH:9]=[N:10]4)=[CH:5][CH:4]=3)=[O:14])[S:21][C:22]=2[CH:28]=1

Participants

5

Reactant 3

HCID 72266-Chloro-2-benzothiazolamineHCID 24387Phosphorus trichlorideHCID 2313638-Hydroxyquinoline-7-carboxylic Acid

Product 1

HCID 18372733N-(6-Chloro-2-benzothiazolyl)-8-hydroxy-7-quinolinecarboxamideYield 54.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 8-hydroxyquinoline-7-carboxylic acid (0.30 g) of Preparation 1 in 75 mL xylenes is heated to reflux. PCl3 (0.07 mL) is added dropwise and the mixture stirred for 15 minutes. 2-Amino-6-chlorobenzothiazole (0.31 g) is added in one portion and the reaction refluxed overnight. The reaction is cooled to room temperature and H2O is added to quench excess PCl3. After stirring the solution for 30 minutes, a yellow solid is filtered, dried, and recrystallized from DMSO to give the title product (0.31 g).

Workup

  1. temperatureis heated to reflux
  2. temperaturethe reaction refluxed overnight
  3. customto quench excess PCl3
  4. stirringAfter stirring the solution for 30 minutes
  5. filtrationa yellow solid is filtered
  6. customdried
  7. customrecrystallized from DMSO

Sources & evidence

ORD record
ord-16d3c32698fa40ed92a53875ed296c77
Source dataset
uspto-grants-2001_10
Patent number
US06310211B1

Linked notes

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