Hydrochloric Acid → 4-Chloro-6-cyclopropyl-1,3,5-triazin-2-amine

HRID 329454Notes

Reaction equation

HRID 329454 reaction equation
[Na].[C:2]([NH:4][C:5]([CH:9]1[CH2:11][CH2:10]1)=[N:6][C:7]#[N:8])#[N:3].[ClH:12].CCCCCC>CC(=O)CC>[NH2:8][C:7]1[N:3]=[C:2]([Cl:12])[N:4]=[C:5]([CH:9]2[CH2:11][CH2:10]2)[N:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 5360545SodiumHCID 19872211N,N′-Dicyanocyclopropanecarboximidamide

Product 1

HCID 198722124-Chloro-6-cyclopropyl-1,3,5-triazin-2-amine

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Conditions

Temperature
10 °C

Procedure

33 g of the sodium salt of N,N'-dicyano-cyclopropanecarbamidine (crude product) is suspended in 100 ml butanone. A solution of 20 g HCl in 400 ml butanone is dropped under stirring into this solution at 10° C. After the addition has been completed it is stirred for 1 h at ambient temperature. The reaction mixture is concentrated by evaporation and 200 ml of saturated aqueous NaHCO3 -solution and 300 ml diethylether are added. The organic phase is separated, washed, dried and concentrated by evaporation. One isolates 21 g of crude product which is treated with hexane to leave the pure title product.

Workup

  1. additionAfter the addition
  2. stirringis stirred for 1 h at ambient temperature
  3. concentrationThe reaction mixture is concentrated by evaporation and 200 ml of saturated aqueous NaHCO3 -solution and 300 ml diethylether
  4. additionare added
  5. customThe organic phase is separated
  6. washwashed
  7. customdried
  8. concentrationconcentrated by evaporation
  9. customOne isolates 21 g of crude product which

Sources & evidence

ORD record
ord-9c52b814efe34122964a2622207880d0
Source dataset
uspto-grants-1990_01
Patent number
US04891443

Reaction notes

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