Phosphorus oxychloride → HCID 18760214, compound

HRID 432665Notes

Reaction equation

HRID 432665 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=O)=[C:6]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:5]([N+:19]([O-:21])=[O:20])=[CH:4][CH:3]=1.O=P(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:7]2[C:8](=[O:10])[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([F:18])[CH:16]=3)[NH:11][C:6]=2[C:5]([N+:19]([O-:21])=[O:20])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 18760211HCID 18760211, compound

Product 1

HCID 18760214HCID 18760214, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 6-chloro-2-[(4-fluorophenyl)amino]-3-nitrobenzoic acid (12.39 g, 0.04 mol), chloroform (100 ml), and POCl3 (60 ml, 0.64 mol) was stirred at reflux for 8 h. Solvents were removed under reduced pressure. To the residue was added 200 ml of a mixture of 1,4-dioxane and water (8:1), and the mixture was acidified with concentrated hydrochloric acid and stirred at reflux for 2 h. Water was added (200 ml) and the precipitate was collected by filtration and crystallized from N,N-dimethylformamide—water to give 10.2 g (87%) of 1b as orange needles: mp 287-291° C. Anal. (C13H6N2O3ClF) C, H, N.

Workup

  1. temperatureat reflux for 8 h
  2. customSolvents were removed under reduced pressure
  3. additionTo the residue was added 200 ml of a mixture of 1,4-dioxane and water (8:1)
  4. stirringstirred
  5. temperatureat reflux for 2 h
  6. additionWater was added (200 ml)
  7. filtrationthe precipitate was collected by filtration
  8. customcrystallized from N,N-dimethylformamide—water

Sources & evidence

ORD record
ord-a0794b40faea4f9ca34140955e48d6e6
Source dataset
uspto-grants-2003_12
Patent number
US06664263B2

Reaction notes

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