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

HRID 27222

Reaction equation

HRID 27222 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].[CH:10]([NH2:13])([CH3:12])[CH3:11].[OH-].[Na+]>C(OCC)(=O)C>[Cl:9][C:8]1[N:1]=[C:2]([Cl:3])[N:4]=[C:5]([NH:13][CH:10]([CH3:12])[CH3:11])[N:7]=1

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 7954Cyanuric chlorideHCID 14798Sodium Hydroxide

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-15 °C

Procedure

A suspension of 369 g of cyanuric chloride in 1000 ml of ethyl acetate is cooled to -15° C. With good stirring, 124 g of isopropylamine are first added dropwise at -20° C. to -10° C. in the course of 21/2 hours, followed by 267 g of a 30% aqueous solution of sodium hydroxide in the course of one hour. The reaction mixture is stirred for a further 11/2 hours at the same temperature, then the organic phase is separated, washed with two 100 ml portions of water and dried over sodium sulphate. The solvent is evaporated, to yield an oil from which the 2,4-dichloro-6-isopropylamino-s-triazine precipitates in crystalline form after stirring with petroleum ether at low temperature. Melting point: 46°-47° C.

Workup

  1. customthe organic phase is separated
  2. washwashed with two 100 ml portions of water
  3. dry with materialdried over sodium sulphate
  4. customThe solvent is evaporated

Sources & evidence

ORD record
ord-32cef9d776e644fa9ed2f82788d54e0e
Source dataset
uspto-grants-1980_09
Patent number
US04220770

Linked notes

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