Sodium → HCID 178484998, compound

HRID 838860Notes

Reaction equation

HRID 838860 reaction equation
[Na].[C:2]([NH:4][C:5]([NH:10][CH3:11])=[N:6][CH2:7][CH2:8][SH:9])#[N:3].Cl.[CH3:13][C:14]1[NH:18][CH:17]=[N:16][C:15]=1[CH2:19]Cl>C(O)C>[C:2]([NH:4][C:5]([NH:10][CH3:11])=[N:6][CH2:7][CH2:8][S:9][CH2:19][C:15]1[N:16]=[CH:17][NH:18][C:14]=1[CH3:13])#[N:3]

Participants

5

Reactant 3

HCID 5360545Sodium2×HCID 124562084-(Chloromethyl)-5-methyl-1H-imidazole--hydrogen chloride (1/1)HCID 178485018HCID 178485018, compound

Product 1

HCID 178484998HCID 178484998, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium (1.43 g) was added, with stirring under nitrogen, to dry ethanol (100 ml). After the sodium had dissolved a solution of N-cyano-N'-methyl-N"-(2-mercaptoethyl)guanidine (4.90 g) in dry ethanol (50 ml) was added and the mixture was stirred at room temperature for one hour. 5-Methyl-4-chloromethylimidazole hydrochloride (5.18 g) was added in batches over a period of 1 hour at room temperature. The mixture was then stirred at room temperature, for a further hour and heated at reflux temperature for 1/2 hour. After cooling the mixture was filtered and the filtrate was evaporated to a glassy solid (8.8 g). This crude product was chromatographed on silica gel with acetonitrile as eluant and the solid product obtained (3.60 g) was recrystallised from acetonitrile to give N-cyano-N'-methyl-N"-[2-(5-methyl-4-imidazolylmethylthio)ethyl]guanidine, m.p. = 140°-142° C.

Workup

  1. additionwas added
  2. stirringThe mixture was then stirred at room temperature, for a further hour
  3. temperatureheated
  4. temperatureat reflux temperature for 1/2 hour
  5. temperatureAfter cooling the mixture
  6. filtrationwas filtered
  7. customthe filtrate was evaporated to a glassy solid (8.8 g)
  8. customThis crude product was chromatographed on silica gel with acetonitrile as eluant
  9. customthe solid product obtained (3.60 g)
  10. customwas recrystallised from acetonitrile

Sources & evidence

ORD record
ord-44d7ce9d0f12445c85d70f9fc759d777
Source dataset
uspto-grants-1978_06
Patent number
US04093621

Reaction notes

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