Atrazine → 1,3,5-Triazin-2-amine, 4,6-dichloro-N-(1-methylethyl)-

HRID 27983

Reaction equation

CCN[C:4]1[N:9]=[C:8]([Cl:10])[N:7]=[C:6]([NH:11][CH:12]([CH3:14])[CH3:13])[N:5]=1.N1C(Cl)=NC(Cl)=NC=1[Cl:17].C(N)(C)C.[OH-].[Na+]>>[Cl:10][C:8]1[N:9]=[C:4]([Cl:17])[N:5]=[C:6]([NH:11][CH:12]([CH3:14])[CH3:13])[N:7]=1

Participants

Reactant 4

HCID 2256Atrazine

HCID 6363Isopropylamine

HCID 7954Cyanuric chloride

HCID 14798Sodium Hydroxide

Product 1

HCID 194531,3,5-Triazin-2-amine, 4,6-dichloro-N-(1-methylethyl)-

Procedure

In particular the preparation of atrazine is generally carried out by a discontinuous method, by reacting, in a first reaction stage, cyanuric chloride with isopropylamine in the presence of sodium hydroxide to give 2,4-dichloro-6-isopropylamino-s-triazine. This latter is reacted, in a second stage, with ethylamine and with a further quantity of sodium hydroxide with the subsequent formation of the desired product: 2-chloro-4-ethylamino-6-isopropylamino-s-triazine.

Sources & evidence

ORD record: ord-eb62d8f6b81d4677ae9c5e38bb79c821
Source dataset: uspto-grants-1980_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04224444

Linked notes

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