Pentafluorobenzoyl chloride → HCID 20451667, compound

HRID 1463079Notes

Reaction equation

HRID 1463079 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12].[F:13][C:14]1[C:22]([F:23])=[C:21]([F:24])[C:20]([F:25])=[C:19]([F:26])[C:15]=1[C:16](Cl)=[O:17]>C(#N)C.CC(C)=O>[F:13][C:14]1[C:22]([F:23])=[C:21]([F:24])[C:20]([F:25])=[C:19]([F:26])[C:15]=1[C:16]([NH:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12])=[O:17]

Participants

5

Reactant 2

HCID 75256Pentafluorobenzoyl chlorideHCID 38948482-Amino-4-chloro-5-nitrophenol

Product 1

HCID 20451667HCID 20451667, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6342AcetonitrileSolvent

Procedure

In 100 ml of acetonitrile was dispersed 18.9 g (0.10 mole) of 2-amino-4-chloro-5-nitrophenol and a solution of 23.1 g (0.10 mole) of 2,3,4,5,6-pentafluorobenzoyl chloride in 50 ml of acetone was added dropwide to the resultant dispersion. After heating under reflux for 3 hours, the reaction mixture was ice-cooled and the precipitated solids were collected by filtration, washed with cooled acetonitrile and dried to obtain 32.5 g of 2-(2,3,4,5,6-pentafluorobenzamido)-4-chloro-5-nitrophenol (Yield 85%).

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 3 hours
  3. temperaturecooled
  4. filtrationthe precipitated solids were collected by filtration
  5. washwashed with cooled acetonitrile
  6. customdried

Sources & evidence

ORD record
ord-60bd688b40a547688f671da95616a47f
Source dataset
uspto-grants-1984_07
Patent number
US04463086

Reaction notes

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