Phosphorus trichloride → HCID 178522602, compound

HRID 1069504Notes

Reaction equation

HRID 1069504 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([C:12]([OH:14])=O)[C:9]([OH:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[NH2:16][C:17]1[S:18][C:19]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[C:20]([OH:22])[N:21]=1.P(Cl)(Cl)Cl>O>[Br:1][C:2]1[CH:11]=[C:10]([C:12]([NH:16][C:17]2[S:18][CH:19]([C:23]3[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=3)[C:20](=[O:22])[N:21]=2)=[O:14])[C:9]([OH:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 3

HCID 24387Phosphorus trichlorideHCID 145347685-Bromo-8-hydroxyquinoline-7-carboxylic acidHCID 183727262-Amino-5-(4-chlorophenyl)-4-thiazolol

Product 1

HCID 178522602HCID 178522602, compoundYield 11.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5-bromo-8-hydroxyquinoline-7-carboxylic acid (0.268 g) of Preparation 2 and 2-amino-5-(4-chlorophenyl)-4-hydroxy-1,3-thiazole (0.227 g) in 50 mL xylenes is heated to reflux. To this is added dropwise PCl3 (0.069 g). Refluxing is continued overnight. The reaction is then cooled and water is added to destroy excess PCl3. The resulting solid is collected, washed with water and dried. The crude product is recrystallized from HOAc to yield 0.055 g of the title product as an orange solid.

Workup

  1. temperatureis heated to reflux
  2. temperatureRefluxing
  3. temperatureThe reaction is then cooled
  4. customto destroy excess PCl3
  5. customThe resulting solid is collected
  6. washwashed with water
  7. customdried
  8. customThe crude product is recrystallized from HOAc

Sources & evidence

ORD record
ord-44e0cd1d5ba2414b9017de336a3ad5be
Source dataset
uspto-grants-2001_06
Patent number
US06252080B1

Reaction notes

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