Ammonia → 2-((4-Amino-6-chloro-1,3,5-triazin-2-yl)oxy)phenol

HRID 972187Notes

Reaction equation

HRID 972187 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5](Cl)=[N:4][C:2]=1Cl.[NH3:10].[C:11]1([C:13](=[CH:15][CH:16]=[CH:17][CH:18]=1)[OH:14])[OH:12]>O.[OH-].[Na+]>[NH2:10][C:2]1[N:1]=[C:8]([Cl:9])[N:7]=[C:5]([O:12][C:11]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[OH:14])[N:4]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 289CatecholHCID 7954Cyanuric chloride

Product 1

HCID 64543042-((4-Amino-6-chloro-1,3,5-triazin-2-yl)oxy)phenol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent5×HCID 14798Sodium HydroxideSolvent2×

Conditions

Temperature
35 °C

Procedure

A suspension of 36.9 parts of cyanuric chloride in 250 parts of water at 0°-5° C was prepared. To the stirred suspension at this temperature were added separately over about 30 minutes a solution of ammonia (3.4 parts) in water (80 parts) concurrently with a solution of sodium hydroxide (8.0 parts) in water (80 parts). Stirring was continued at 0°-5° C for about 90 minutes after completion of the addition. The temperature of the mixture was then increased to 35° C and solutions of catechol (22 parts) in water (180 parts) and sodium hydroxide (8 parts) in water (70 parts) were added with stirring at this temperature over about 40 minutes. Stirring was continued for about 1 hour at 35° C when the reaction reached neutrality. The reaction mixture was cooled to 10° C and the product isolated by filtration, washed with water and dried. 2-amino-4-chloro-6 -(2'-hydroxyphenoxy)-s-triazine was thereby obtained as an off-white powder of indefinite melting point due to decomposition, analysing for carbon 43.2%, hydrogen 2.6%, nitrogen 23.2% and chlorine 14.3%. (C9H7ClN4O2 requires carbon 45.3%, hydrogen 2.9%, nitrogen 23.5% and chlorine 14.9%).

Workup

  1. customwas prepared
  2. additionafter completion of the addition
  3. stirringwith stirring at this temperature over about 40 minutes
  4. stirringStirring
  5. waitwas continued for about 1 hour at 35° C
  6. temperatureThe reaction mixture was cooled to 10° C
  7. customthe product isolated by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-6a57544de22c4e39b17a9257f136a069
Source dataset
uspto-grants-1977_10
Patent number
US04052392

Reaction notes

Loading…