Water → 3-(3,5-Dichloropyrid-2-yloxy)-4-methoxyaniline

HRID 652065Notes

Reaction equation

HRID 652065 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH3:10])=[C:6]([OH:8])[CH:7]=1.[OH-].[K+].O.Cl[C:15]1[C:20]([Cl:21])=[CH:19][C:18]([Cl:22])=[CH:17][N:16]=1>C1(C)C=CC=CC=1.CS(C)=O.C(O)(=O)C>[Cl:21][C:20]1[C:15]([O:8][C:6]2[CH:7]=[C:2]([CH:3]=[CH:4][C:5]=2[O:9][CH3:10])[NH2:1])=[N:16][CH:17]=[C:18]([Cl:22])[CH:19]=1

Participants

8

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 27666Pyridine, 2,3,5-trichloro-HCID 743145-Amino-2-methoxyphenol

Product 1

HCID 140533363-(3,5-Dichloropyrid-2-yloxy)-4-methoxyanilineYield 98.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 14.0 g (0.1 mol) of 5-amino-2-methoxyphenol and 6.7 g (0.1 mol) of potassium hydroxide (85%) in 100 ml of toluene and 100 ml of dimethyl sulfoxide is dewatered at 150° C. in a sulfonating flask equipped with a water separator. After 3 hours the toluene is distilled off, the mixture is cooled to 80° C. and 18.2 g (0.1 mol) of 2,3,5-trichloropyridine in 25 ml of dimethyl sulfoxide are added. The mixture is stirred for 3 hours at 120° C. and then cooled and 5 ml of acetic acid are added. After distillation under a high vacuum, the residue is extracted with 200 ml of water and 300 ml of methylene chloride. The organic phase affords 28 g of 3-(3,5-dichloropyrid-2-yloxy)-4-methoxyaniline as congealing oil. Melting point 95°-105° C.

Workup

  1. customis dewatered at 150° C. in a sulfonating flask
  2. distillationAfter 3 hours the toluene is distilled off
  3. temperaturecooled
  4. distillationAfter distillation under a high vacuum
  5. extractionthe residue is extracted with 200 ml of water and 300 ml of methylene chloride

Sources & evidence

ORD record
ord-c8fccb44032c4e658cef8e92b7eef001
Source dataset
uspto-grants-1987_06
Patent number
US04670441

Reaction notes

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