Cyclopropylamine → N~2~,N~4~,N~6~-Tricyclopropyl-1,3,5-triazine-2,4,6-triamine

HRID 1448778Notes

Reaction equation

HRID 1448778 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:11][CH2:10]2)[N:5]=[C:4]([NH:12][CH:13]2[CH2:15][CH2:14]2)[N:3]=1.[CH:16]1([NH2:19])[CH2:18][CH2:17]1>O1CCOCC1>[CH:16]1([NH:19][C:2]2[N:7]=[C:6]([NH:8][CH:9]3[CH2:11][CH2:10]3)[N:5]=[C:4]([NH:12][CH:13]3[CH2:15][CH2:14]3)[N:3]=2)[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 6430808HCID 6430808, compound

Product 1

HCID 57290175N~2~,N~4~,N~6~-Tricyclopropyl-1,3,5-triazine-2,4,6-triamine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 20 g of 2-chloro-4,6-bis-cyclopropylamino-s-triazine, 10.1 g of cyclopropylamine and 80 ml of dioxan is heated at 140° C. in an autoclave for 22 hours. The reaction mixture is concentrated in vacuo to half its volume and 300 ml of water are added. The mixture is extracted with ethyl acetate, the product phase is dried over sodium sulfate and the solvents are removed in vacuo. The residue is recrystallised from dioxan/petroleum ether; melting point 75°-77° C.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo to half its volume and 300 ml of water
  2. additionare added
  3. extractionThe mixture is extracted with ethyl acetate
  4. dry with materialthe product phase is dried over sodium sulfate
  5. customthe solvents are removed in vacuo
  6. customThe residue is recrystallised from dioxan/petroleum ether

Sources & evidence

ORD record
ord-be9ceb9e994d444193d71bfb373bd838
Source dataset
uspto-grants-1980_02
Patent number
US04187305

Reaction notes

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