Ethylamine → Atrazine

HRID 2052104Notes

Reaction equation

HRID 2052104 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][CH:10]([CH3:12])[CH3:11])[N:3]=1.[CH2:13]([NH2:15])[CH3:14].[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:8][C:6]1[N:7]=[C:2]([NH:15][CH2:13][CH3:14])[N:3]=[C:4]([NH:9][CH:10]([CH3:12])[CH3:11])[N:5]=1

Participants

5

Reactant 3

HCID 6341EthylamineHCID 14798Sodium HydroxideHCID 194531,3,5-Triazin-2-amine, 4,6-dichloro-N-(1-methylethyl)-

Product 1

HCID 2256Atrazine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To the solution of 2,4-dichloro-6-isopropylamino-s-triazine in toluene remaining in the reactor are added, under strong agitation, about 915 g of an aqueous solution containing 50% by weight of ethylamine (10.15 moles) and about 1353 g of an aqueous solution containing 30% by weight of sodium hydroxide (10.15 moles). The said solutions are added in the same manner as in the first reaction step. During the second addition the temperature rises from 25° to 50° C. and the final pH is equal to 11.-12. The dense suspension thus obtained is divided into two parts as quickly as possible. One part (A) is submitted to distillation to remove the toluene in the form of an azeotropic toluene-water mixture, by operating at 85°-100° C. To the distillation residue are added 3,700 ml of water and the suspension thus obtained is filtered at 60° C. The filtered solid is washed until the sodium chloride has been removed completely. After drying for ten hours in an oven at 100° C., 2-chloro-4-ethylamino-6-isopropylamino-s-triazine is obtained with a yield of the orde of 96%.

Workup

  1. additionThe said solutions are added in the same manner as in the first reaction step
  2. additionDuring the second addition the temperature
  3. customrises from 25° to 50° C.
  4. customThe dense suspension thus obtained
  5. distillationOne part (A) is submitted to distillation
  6. customto remove the toluene in the form of an azeotropic toluene-water mixture
  7. customby operating at 85°-100° C
  8. additionTo the distillation residue are added 3,700 ml of water
  9. customthe suspension thus obtained
  10. filtrationis filtered at 60° C
  11. washThe filtered solid is washed until the sodium chloride
  12. customhas been removed completely
  13. customAfter drying for ten hours in an oven at 100° C.

Sources & evidence

ORD record
ord-65238ece68054bcaae5c50dac689ef61
Source dataset
uspto-grants-1980_01
Patent number
US04182874

Reaction notes

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