Potassium Cyanide → 2-{[Cyano-(2,3,5-trichlorophenyl)methyl]-amino}acetamidine Hydrobromide

HRID 392855Notes

Reaction equation

HRID 392855 reaction equation
[C-:1]#[N:2].[K+].[BrH:4].Br.[NH2:6][CH2:7][C:8]([NH2:10])=[NH:9].[Cl:11][C:12]1[C:19]([Cl:20])=[CH:18][C:17]([Cl:21])=[CH:16][C:13]=1[CH:14]=O>CO>[BrH:4].[C:1]([CH:14]([NH:6][CH2:7][C:8]([NH2:10])=[NH:9])[C:13]1[CH:16]=[C:17]([Cl:21])[CH:18]=[C:19]([Cl:20])[C:12]=1[Cl:11])#[N:2]

Participants

5

Reactant 3

HCID 9032Potassium Cyanide2×HCID 925962,3,5-TrichlorobenzaldehydeHCID 16211382Aminoacetamidine Dihydrobromide

Product 1

HCID 693443222-{[Cyano-(2,3,5-trichlorophenyl)methyl]-amino}acetamidine Hydrobromide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

Potassium cyanide (6.1 Kg) was dissolved in methanol (119 Kg) at 50° C. over 1 hour. Aminoacetamidine dihydrobromide (19.6 Kg) was added to the potassium cyanide solution in one portion and stirred at 25° C. for 15 minutes to allow formation of the mono acid mono hydrocyanide salt. Subsequently, 2,3,5-trichlorobenzaldehyde (24.2 Kg) was added to the reaction mixture in one portion and the mixture was stirred at 50° C. for 16 hours. On cooling to 25° C., vacuum was applied and the mixture concentrated to 5 volumes. Isopropyl ether (145 Kg) was added over 30 minutes and the mixture stirred at 20° C. overnight. The crude product was isolated by filtration and the cake washed with isopropyl ether (43 Kg). The crude product was slurried with ethyl acetate (158 kg). and water (100 kg) overnight at 20° C. The product was isolated by filtration washed with water (50 Kg), ethyl acetate (90 Kg) and vacuum dried at 400C to afford 2-{[Cyano-(2,3,5-trichlorophenyl)-methyl]-amino}-acetamidine hydrobromide. Yield 17.43 Kg (50% -92% w/w assay). HPLC retention time 3.9 minutes.

Workup

  1. stirringthe mixture was stirred at 50° C. for 16 hours
  2. temperatureOn cooling to 25° C.
  3. concentrationthe mixture concentrated to 5 volumes
  4. additionIsopropyl ether (145 Kg) was added over 30 minutes
  5. stirringthe mixture stirred at 20° C. overnight
  6. customThe crude product was isolated by filtration
  7. washthe cake washed with isopropyl ether (43 Kg)
  8. customwater (100 kg) overnight
  9. customat 20° C
  10. customThe product was isolated by filtration
  11. washwashed with water (50 Kg), ethyl acetate (90 Kg) and vacuum
  12. dry with materialdried at 400C

Sources & evidence

ORD record
ord-20423715331d4183b1fd6468c4051e6e
Source dataset
uspto-grants-2004_10
Patent number
US06803464B2

Reaction notes

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