Cyanamide → HCID 178485068, compound

HRID 1702483Notes

Reaction equation

HRID 1702483 reaction equation
CN=C(Cl)Cl.CC1NC=NC=1CSCCN.C1CCN2C(=NCCC2)CC1.[CH3:28][N:29]=[C:30](Cl)[NH:31][CH2:32][CH2:33][S:34][CH2:35][C:36]1[N:37]=[CH:38][NH:39][C:40]=1[CH3:41].[N:43]#[C:44][NH2:45]>C(Cl)Cl>[C:44]([N:45]=[C:30]([NH:31][CH2:32][CH2:33][S:34][CH2:35][C:36]1[N:37]=[CH:38][NH:39][C:40]=1[CH3:41])[NH:29][CH3:28])#[N:43]

Participants

7

Reactant 5

HCID 9864CyanamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 12647927N-methyl-chloroformimidoyl chlorideHCID 20504046N'-methyl-N-[2-(5-methylimidazol-4-ylmethylthio)ethyl]chloroformamidine

Product 1

HCID 178485068HCID 178485068, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of N-methyl-chloroformimidoyl chloride (1.12 g), 2-(5-methylimidazol-4-ylmethylthio)ethylamine (0.855 g) and DBU (0.988 g) in CH2Cl2 (16 ml was heated under reflux for 6 hrs. To the reaction mixture containing N'-methyl-N-[2-(5-methylimidazol-4-ylmethylthio)ethyl]chloroformamidine was added a solution of cyanamide (0.84 g) and DBU (3.04 g) in CH2Cl2 (16 ml). After refluxing for 15 hrs., the solvent was removed and the residue was chromatographed [SiO2, CH3CN-CH3OH (4:1)]. The crude product was purified by preparative chromatography [SiO2, CH3COOC2H5 --CH3OH-- 28% NH3 (aq) (10:1:1)] and then recrystallization from CH3CN to give N"-cyano-N-methyl-N'-[2-(5-methylimidazol-4-ylmethylthio)ethyl]guanidine (0.24 g). Yield 19.0%, m.p. 139°-141° C.

Workup

  1. temperatureunder reflux for 6 hrs
  2. temperatureAfter refluxing for 15 hrs
  3. custom, the solvent was removed
  4. customthe residue was chromatographed [SiO2, CH3CN-CH3OH (4:1)]
  5. customThe crude product was purified by preparative chromatography [SiO2, CH3COOC2H5 --CH3OH-- 28% NH3 (aq) (10:1:1)]
  6. customrecrystallization from CH3CN

Sources & evidence

ORD record
ord-5496a29136d64303aa928b62eb5cb79d
Source dataset
uspto-grants-1983_04
Patent number
US04381395

Reaction notes

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