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

HRID 1069505Notes

Reaction equation

HRID 1069505 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-63d62fa3266e45e7ae0d34634ba61968
Source dataset
uspto-grants-2001_06
Patent number
US06252080B1

Reaction notes

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