5-(2-Chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoyl chloride → 1-[5-(2-Chloro-4-trifluoromethylphenoxy)-2-nitrobenzamido]pyridinium chloride

HRID 746149

Reaction equation

HRID 746149 reaction equation
[Cl-].[NH2:2][N+:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:9][C:10]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:11]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([N+:22]([O-:24])=[O:23])=[C:17]([CH:21]=1)[C:18](Cl)=[O:19]>C(#N)C>[Cl-:9].[Cl:9][C:10]1[CH:28]=[C:27]([C:29]([F:30])([F:32])[F:31])[CH:26]=[CH:25][C:11]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([N+:22]([O-:24])=[O:23])=[C:17]([CH:21]=1)[C:18]([NH:2][N+:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:19]

Participants

4

Reactant 2

HCID 30177655-(2-Chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoyl chlorideHCID 12210597HCID 12210597, compound

Product 1

HCID 202407781-[5-(2-Chloro-4-trifluoromethylphenoxy)-2-nitrobenzamido]pyridinium chlorideYield 156.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Aminopyridinium chloride (2.9 g) was added to 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoyl chloride (7.6 g) in acetonitrile (50 ml). The mixture was stirred and heated to reflux. After 20 minutes a solid precipitated. Reflux was continued for a further 40 minutes. Then the mixture was cooled in ice and the solid filtered off. The solid was washed with cold acetonitrile, then with ether, and was air dried to give 7.4 g of the desired product, mp 234°-237° C.

Workup

  1. temperatureheated to reflux
  2. customAfter 20 minutes a solid precipitated
  3. temperatureReflux
  4. temperatureThen the mixture was cooled in ice
  5. filtrationthe solid filtered off
  6. washThe solid was washed with cold acetonitrile
  7. customdried

Sources & evidence

ORD record
ord-4593eaa837e64527a44451757e68ee7b
Source dataset
uspto-grants-1986_07
Patent number
US04602944

Linked notes

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