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

HRID 1633471Notes

Reaction equation

[BrH:1].Br.[NH2:3][CH2:4][C:5]([NH2:7])=[NH:6].[Cl:8][C:9]1[C:16]([Cl:17])=[CH:15][C:14]([Cl:18])=[CH:13][C:10]=1[CH:11]=O.[C-:19]#[N:20].[K+]>CO>[BrH:1].[C:19]([CH:11]([NH:3][CH2:4][C:5]([NH2:7])=[NH:6])[C:10]1[CH:13]=[C:14]([Cl:18])[CH:15]=[C:16]([Cl:17])[C:9]=1[Cl:8])#[N:20]

Participants

Conditions

Temperature: 25 °C

Procedure

Aminoacetamidine dihydrobromide (162.1 g, 0.774 mole) was added in portions to a solution of 2,3,5-trichlorobenzaldehyde (200.0 g, 0.851 mole) in methanol (2.43 litres) at room temperature. Once the addition was complete potassium cyanide (50.4 g, 0.774 mole) was added in one portion to the resulting mixture. The suspension was then stirred at 25° C. for 4 hours before being warmed to 50° C. The mixture is stirred at 50° C. for 24 hours. Methanol was then removed in vacuo, the resulting solid was slurried in water (1.5 litres) and ethyl acetate (2.5 litres) and collected by filtration. The solid was then dried in vacuo at 50° C. overnight to give the desired product. Yield 96.31 g (33.4%), 1H nmr (d-6 DMSO) δ/ppm 8.72 (3H, br, NH); 7.99 (1H, d, J 2.3 Hz, ArH); 7.79 (1H, d, J 2.3 Hz, ArH); 5.39 (1H, d, J 10.6 Hz, ArCH(CN)NH); 4.35 (1H, m, ArCH(CN)NH); 3.56 (2H, d, J 6.4 Hz, ArCH(CN)NHCH2C(═NH)NH2).

Workup

additionOnce the addition
additionwas added in one portion to the resulting mixture
temperaturebefore being warmed to 50° C
stirringThe mixture is stirred at 50° C. for 24 hours
customMethanol was then removed in vacuo
filtrationethyl acetate (2.5 litres) and collected by filtration
customThe solid was then dried in vacuo at 50° C. overnight

Sources & evidence

ORD record: ord-23ea517c51a34ca09eea2a9e9542f5a7
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06503909B1

Reaction notes

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