Phosphorus trichloride → HCID 178522603, compound

HRID 382864Notes

Reaction equation

HRID 382864 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.[NH2:15][C:16]1[S:17][C:18]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[C:19]([OH:21])[N:20]=1.P(Cl)(Cl)Cl>O>[Cl:28][C:25]1[CH:24]=[CH:23][C:22]([CH:18]2[S:17][C:16]([NH:15][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:20][C:19]2=[O:21])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 24387Phosphorus trichlorideHCID 2313638-Hydroxyquinoline-7-carboxylic AcidHCID 183727262-Amino-5-(4-chlorophenyl)-4-thiazolol

Product 1

HCID 178522603HCID 178522603, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 8-hydroxyquinoline-7-carboxylic acid (0.280 g) of Preparation 1 and 2-amino-5-(4-chlorophenyl)-4-hydroxy-1,3-thiazole (0.340 g) in 50 mL xylenes is heated to reflux. To this is added dropwise PCl3 (0.103 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 triturated with HOAc to yield 0.236 g of the title product as a gold 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 triturated with HOAc

Sources & evidence

ORD record
ord-46ae3cf0020f4d02969a68bade4ea9e8
Source dataset
uspto-grants-2001_10
Patent number
US06310211B1

Reaction notes

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