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

HRID 2301419Notes

Reaction equation

HRID 2301419 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-aceefc87892b4770871d0f7fd0f8ae7e
Source dataset
uspto-grants-2002_12
Patent number
US06500842B1

Reaction notes

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