Ethylamine → Atrazine

HRID 1862893Notes

Reaction equation

HRID 1862893 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5](Cl)=[N:4][C:2]=1Cl.[CH:10]([NH2:13])([CH3:12])[CH3:11].[OH-].[Na+].[CH2:16]([NH2:18])[CH3:17]>CC(C)=O.O>[CH3:17][CH2:16][NH:18][C:2]1[N:1]=[C:8]([Cl:9])[N:7]=[C:5]([NH:13][CH:10]([CH3:12])[CH3:11])[N:4]=1

Participants

7

Reactant 4

HCID 6341EthylamineHCID 6363Isopropylamine2×HCID 7954Cyanuric chloride3×HCID 14798Sodium Hydroxide3×

Product 1

HCID 2256Atrazine

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent3×

Conditions

Temperature
35 °C

Procedure

Using the apparatus and general procedure described in Illustrative Embodiment IA, a 30.5% by weight solution of cyanuric chloride in acetone was charged to a batch reaction vessel. A less than stoichiometric amount of isopropylamine (the molar ratio of cyanuric chloride to isopropylamine was 1.04) was charged over a period of one hour and then sufficient 20% by weight sodium hydroxide in water was added over a period of 40 minutes to bring the pH of the aqueous phase to 8.0. The temperature of the reaction mixture during both reaction steps was controlled at 10° C. Hydrolysis of the excess cyanuric chloride was effected by reducing the pH to 6.0 and heating the reaction mixture to 35° C. for a period of 0.5 hours. Aqueous sodium hydroxide solution was added as necessary to maintain the pH of the reaction mixture at 6.0. At the conclusion of this reaction step, the pH was increased to 8.0 and ethylamine as a 68% solution in water was added over a period of 30 minutes. Sufficient 20% by weight sodium hydroxide solution was added over a period of 45 minutes to produce a pH of 8.5. The temperature of the reaction mixture was maintained at 35° C. during this reaction sequence. Crude atrazine was isolated from the reaction mixture by precipitation with water. The molar yield of atrazine was 94.3% based on isopropylamine charged to the reaction. The composition of the crude atrazine was determined by gas-liquid chromatography and is given below.

Workup

  1. additionwas charged over a period of one hour
  2. customThe temperature of the reaction mixture during both reaction steps
  3. customwas controlled at 10° C
  4. temperatureto maintain the pH of the reaction mixture at 6.0
  5. customAt the conclusion of this reaction step
  6. additionwas added over a period of 30 minutes
  7. customto produce a pH of 8.5
  8. temperatureThe temperature of the reaction mixture was maintained at 35° C. during this reaction sequence

Sources & evidence

ORD record
ord-315ae2488a1a4113bcf2b0ecef92885d
Source dataset
uspto-grants-1979_09
Patent number
US04166909

Reaction notes

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