2,4-Dichlorophenol → HCID 20261995, compound

HRID 463602Notes

Reaction equation

HRID 463602 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].[CH3:16][C:17]([NH:19][C:20]1[CH:25]=[C:24](F)[CH:23]=[CH:22][C:21]=1[N+:27]([O-:29])=[O:28])=[O:18]>CS(C)=O.O>[CH3:16][C:17]([NH:19][C:20]1[CH:25]=[C:24]([O:9][C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[CH:23]=[CH:22][C:21]=1[N+:27]([O-:29])=[O:28])=[O:18]

Participants

6

Reactant 3

HCID 84492,4-DichlorophenolHCID 11430Potassium CarbonateHCID 16641156N-(5-Fluoro-2-nitrophenyl)acetamide

Product 1

HCID 20261995HCID 20261995, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 2,4-dichlorophenol (1.2 g, 7.6 mmol) and potassium carbonate (2.1 g, 15.2 mmol) is stirred together in dimethylsulfoxide (20 ml). N-methylcarbonyl 2-nitro-5-fluoroaniline (1.5 g, 7.6 mmol) is added in portions. After 1 hour, the reaction is heated to 100° for 1.5 hours. The reaction is then cooled to RT and diluted with water. A solid is collected, dissolved in chloroform, washed with water, dried and stripped to give N-methylcarbonyl 2-nitro-5-(2,4-dichlorophenoxy)aniline.

Workup

  1. temperaturethe reaction is heated to 100° for 1.5 hours
  2. customA solid is collected
  3. dissolutiondissolved in chloroform
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-35dd7a773c65457bb925f0ad1b6e08f7
Source dataset
uspto-grants-1985_10
Patent number
US04544400

Reaction notes

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