Phosphorus trichloride → N-[5-(5-Bromo-2-thienyl)-2-thiazolyl]-8-hydroxy-7-quinolinecarboxamide

HRID 2301413Notes

Reaction equation

HRID 2301413 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]([C:25]2[S:26][C:27]([Br:30])=[CH:28][CH:29]=2)=[CH:23][N:24]=1>O>[Br:30][C:27]1[S:26][C:25]([C:22]2[S:21][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])=[N:24][CH:23]=2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 24387Phosphorus trichlorideHCID 2313638-Hydroxyquinoline-7-carboxylic AcidHCID 183726572-Amino-5-(5-bromothien-2-yl)thiazole

Product 1

HCID 18372556N-[5-(5-Bromo-2-thienyl)-2-thiazolyl]-8-hydroxy-7-quinolinecarboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 8-hydroxyquinoline-7-carboxylic acid (0.43 g) of Preparation 1 in 80 mL xylenes is heated to reflux. PCl3 (0.12 mL) is added dropwise and the mixture stirred for 20 minutes. 2-Amino-5-(5-bromothien-2-yl)thiazole (0.62 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. The solvents are removed and the residue is dissolved in acetic acid. A dark orange solid precipitates upon addition of hexanes (0.28 g) to yield the title product.

Workup

  1. temperatureis heated to reflux
  2. temperaturethe reaction refluxed overnight
  3. customto quench excess PCl3
  4. customThe solvents are removed
  5. dissolutionthe residue is dissolved in acetic acid
  6. customA dark orange solid precipitates upon addition of hexanes (0.28 g)

Sources & evidence

ORD record
ord-0d7de7bfb92a4fc4b524d6004d9f6a87
Source dataset
uspto-grants-2002_12
Patent number
US06500842B1

Reaction notes

Loading…