1609-06-9

Usage

Uses

Used in Pharmaceutical Industry:
Guanidine,N'-cyano-N,N-dimethylis used as an impurity in the production of Cimetidine, which is a competitive histamine H2-receptor antagonist. The application reason for Guanidine,N'-cyano-N,N-dimethylin this context is that it is a byproduct formed during the synthesis of Cimetidine.
Cimetidine is used for its ability to inhibit gastric acid secretion and reduce pepsin output, making it a valuable drug for treating conditions such as peptic ulcers, gastroesophageal reflux disease (GERD), and other acid-related disorders. The presence of Guanidine,N'-cyano-N,N-dimethylas an impurity in Cimetidine is important to monitor and control, as it can potentially affect the safety and efficacy of the drug.

Synthetic route

N,N-dimethylammonium chloride (506-59-2) + sodium dicyanamide (1934-75-4) → N-cyano-N’,N’-dimethylguanidine (1609-06-9)

Conditions	Yield
With butan-1-ol

N-Cyanoguanidine (127099-85-8, 780722-26-1) + dimethyl sulfate (77-78-1) → N-cyano-N’,N’-dimethylguanidine (1609-06-9)

Conditions	Yield
With sodium hydrogencarbonate In methanol

potassium dicyanamide (34723-47-2) + methylamine (74-89-5) → N-cyano-N’,N’-dimethylguanidine (1609-06-9)

Conditions	Yield
In butan-1-ol Heating;

N,N-dimethylammonium chloride (506-59-2) + sodium dicyanamide → N-cyano-N’,N’-dimethylguanidine (1609-06-9)

Conditions	Yield
With butan-1-ol

sodium dicyanamide (1934-75-4) + dimethyl amine (124-40-3) → N-cyano-N’,N’-dimethylguanidine (1609-06-9)

N-cyano-N’,N’-dimethylguanidine (1609-06-9) → C2H4N4O*0.1C2H7N

Conditions	Yield
With hydroxylamine hydrochloride; triethylamine In ethanol at 20℃;	78%

N-cyano-N’,N’-dimethylguanidine (1609-06-9) + 3-chloroaniline hydrochloride (141-85-5) → N,N-dimethyl-(3-chlorophenyl)biguanidine hydrochloride

Conditions	Yield
In water for 2h; Heating;	70%

N-cyano-N’,N’-dimethylguanidine (1609-06-9) + dichloromethylenedimethyliminium chloride (33842-02-3, 529510-96-1) → 2-chloro-4,6-bis(dimethylamino)-1,3,5-triazine (3140-74-7)

Conditions	Yield
In acetonitrile for 0.5h; Heating;	69%

pyridine (110-86-1) + N-cyano-N’,N’-dimethylguanidine (1609-06-9) + N-methoxylamine hydrochloride (593-56-6) → 0.6C5H5N*C5H13N5O

Conditions	Yield
In ethanol for 6h; Reflux;	66%

N-cyano-N’,N’-dimethylguanidine (1609-06-9) + 2-(6-fluoro-1H-indol-3-yl)ethan-1 -amine hydrochloride → 3-(2-(6-fluoro-1H-indol-3-yl)ethyl)-1,1-dimethyimidodicarbonimide diamide hydrochloride

Conditions	Yield
Inert atmosphere; Heating;	46%

N-cyano-N’,N’-dimethylguanidine (1609-06-9) + benzyl alcohol (100-51-6) → 3-(benzylformimidate)-1,1-dimethyl guanide hydrochloride

Conditions	Yield
With hydrogenchloride In water for 18h; Reflux;	40%

2-phenylpropylamine (582-22-9) + N-cyano-N’,N’-dimethylguanidine (1609-06-9) → N-1-(2-phenyl)propane-N-5-dimethylbiguanide hydrochloride

Conditions	Yield
With hydrogenchloride In water; butan-1-ol for 1h; Reflux;	38.8%

N-cyano-N’,N’-dimethylguanidine (1609-06-9) + 5-Fluorotryptamine hydrochloride (2711-58-2) → 3-(2-(5-fluoro-1H-indol-3-yl)ethyl)-1,1-dimethyimidodicarbonimide diamide hydrochloride

Conditions	Yield
Inert atmosphere; Heating;	25%

N-cyano-N’,N’-dimethylguanidine (1609-06-9) + 2-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethan-1-amine hydrochloride (1417567-47-5) + trifluoroacetic acid (76-05-1) → 1-(2-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethyl)-1,1-dimethylimidodicarbonimide diamide trifluoroacetic acid salt

Conditions	Yield
Stage #1: N-cyano-N’,N’-dimethylguanidine; 2-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethan-1-amine hydrochloride Inert atmosphere; Heating; Stage #2: trifluoroacetic acid	7%

N-cyano-N’,N’-dimethylguanidine (1609-06-9) + C20H33NO → C24H41N5O

Conditions	Yield
With hydrogenchloride In water; butan-1-ol for 12h; Reflux;	3.6%

N-cyano-N’,N’-dimethylguanidine (1609-06-9) + N-propylamine hydrochloride (556-53-6) → 1,1-dimethyl-5-propyl-biguanide

Conditions	Yield
at 150℃;

N-cyano-N’,N’-dimethylguanidine (1609-06-9) + methylamine hydrochloride (593-51-1) → 1,1,5-trimethyl-biguanide (101580-27-2)

N-cyano-N’,N’-dimethylguanidine (1609-06-9) + ethanamine hydrochloride (557-66-4) → 5-ethyl-1,1-dimethyl-biguanide (101720-82-5)

N-cyano-N’,N’-dimethylguanidine (1609-06-9) + 5-chloro-2-methyl-aniline; hydrochloride (6259-42-3) → 5-(5-chloro-2-methyl-phenyl)-1,1-dimethyl-biguanide (99981-08-5)

Conditions	Yield
With water

N-cyano-N’,N’-dimethylguanidine (1609-06-9) + n-butylamine hydrochloride (3858-78-4) → 5-butyl-1,1-dimethyl-biguanide

N-cyano-N’,N’-dimethylguanidine (1609-06-9) + isoamylamine hydrochloride (541-23-1) → 5-isopentyl-1,1-dimethyl-biguanide

Conditions	Yield
at 150℃;

N-cyano-N’,N’-dimethylguanidine (1609-06-9) → (N,N'-dimethylamidino)thiourea (34678-04-1)

Conditions	Yield
With hydrogen sulfide In methanol

N-cyano-N’,N’-dimethylguanidine (1609-06-9) + benzohydroximoyl chloride (698-16-8) → N,N-dimethyl-N'-(3-phenyl-[1,2,4]oxadiazol-5-yl)-guanidine (5379-65-7)

Conditions	Yield
In ethanol

N-cyano-N’,N’-dimethylguanidine (1609-06-9) + N,N-dimethylphenylchloromethyleneammonium dichlorophosphate → 4-chloro-2-dimethylamino-6-phenyl-1,3,5-triazine (36323-70-3)

Conditions	Yield
In chloroform for 4h; Heating; Yield given;

N-cyano-N’,N’-dimethylguanidine (1609-06-9) + 3-(undecanyloxy)aniline hydrochloride (65972-29-4) → C21H37N5O

Conditions	Yield
In acetone Heating;

N-cyano-N’,N’-dimethylguanidine (1609-06-9) + allylamine hydrochloride → 5-allyl-1,1-dimethyl-biguanide (102163-20-2)

N-cyano-N’,N’-dimethylguanidine (1609-06-9) + pentylamine hydrochloride → 1,1-dimethyl-5-pentyl-biguanide

Conditions	Yield
at 150℃;

N-cyano-N’,N’-dimethylguanidine (1609-06-9) + 2-(5-trifluoromethyl-1H-indol-3-yl)ethan-1-amine hydrochloride → 3-(2-(5-trifluoromethyl-1H-indol-3-yl)ethyl)-1,1-dimethylimidodicarbonimide diamide hydrochloride

Conditions	Yield
at 170℃; for 3h; Inert atmosphere;	120 mg

Upstream product

• 506-59-2 N,N-dimethylammonium chloride 
• 1934-75-4 sodium dicyanamide 
• 127099-85-8 N-Cyanoguanidine 
• 77-78-1 dimethyl sulfate 
• 34723-47-2 potassium dicyanamide 
• 74-89-5 methylamine 
• 124-40-3 dimethyl amine 

Downstream Products

• 99981-08-5 5-(5-chloro-2-methyl-phenyl)-1,1-dimethyl-biguanide 
• 5379-65-7 3-Phenyl-5-<Ω-(dimethyl-guanidino>-1,2,4-oxadiazol 
• 3140-74-7 2-chloro-4,6-bis(dimethylamino)-1,3,5-triazine 
• 36323-70-3 4-chloro-2-dimethylamino-6-phenyl-1,3,5-triazine 

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