Sodium → N-methyl-N1-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]-thiourea

HRID 597237Notes

Reaction equation

HRID 597237 reaction equation
[CH3:1][N:2]([CH2:6][CH2:7][SH:8])[C:3]([NH2:5])=[S:4].[Na].Cl.Cl[CH2:12][C:13]1[N:14]=[CH:15][NH:16][C:17]=1[CH3:18]>C(O)C>[CH3:1][N:2]([CH2:6][CH2:7][S:8][CH2:12][C:13]1[N:14]=[CH:15][NH:16][C:17]=1[CH3:18])[C:3]([NH2:5])=[S:4]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 124562084-(Chloromethyl)-5-methyl-1H-imidazole--hydrogen chloride (1/1)HCID 54182305N-Methyl-N1-(2-mercaptoethyl)thiourea

Product 1

HCID 21436375N-methyl-N1-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]-thioureaYield 51.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

N-Methyl-N1 -(2-mercaptoethyl)thiourea (3.85 g) in dry ethanol (10 ml) was added to a solution of sodium (1.18 g) in dry ethanol (50 ml) and the mixture was stirred at room temperature for 1 hour. 4-Chloromethyl-5-methylimidazole hydrochloride (4.29 g) was added portionwise over one hour to this stirred mixture at room temperature. The mixture was stirred at room temperature for a further hour and heated under reflux for 1/2 hour, cooled and filtered. The filtrate was evaporated to an oily solid which was recrystallised from water to give N-methyl-N1 -[2-((5-methyl-4-imidazolyl)methylthio)ethyl]-thiourea (3.2 g) m.p. 149°-151° C.

Workup

  1. stirringThe mixture was stirred at room temperature for a further hour
  2. temperatureheated
  3. temperatureunder reflux for 1/2 hour
  4. temperaturecooled
  5. filtrationfiltered
  6. customThe filtrate was evaporated to an oily solid which
  7. customwas recrystallised from water

Sources & evidence

ORD record
ord-2eeff598e7494439b49f7fd6498fc98b
Source dataset
uspto-grants-1977_03
Patent number
US04013678

Reaction notes

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