Water → 1-(2-Chloro-5-thiazolylmethyl)-1-cyano-3,3-dimethyl-2-nitroguanidine

HRID 1657030Notes

Reaction equation

HRID 1657030 reaction equation
[H-].[Na+].[Cl:3][C:4]1[S:5][C:6]([CH2:9][NH:10][C:11]([N:16]([CH3:18])[CH3:17])=[N:12][N+:13]([O-:15])=[O:14])=[CH:7][N:8]=1.[N:19]#[C:20]Br.O>CN(C=O)C.CC#N>[Cl:3][C:4]1[S:5][C:6]([CH2:9][N:10]([C:20]#[N:19])[C:11]([N:16]([CH3:18])[CH3:17])=[N:12][N+:13]([O-:15])=[O:14])=[CH:7][N:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 24758Sodium hydrideHCID 136218199N-(2-chloro-5-thiazolylmethyl)-N',N'-dimethyl-N"-nitroguanidine

Product 1

HCID 541565521-(2-Chloro-5-thiazolylmethyl)-1-cyano-3,3-dimethyl-2-nitroguanidine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To a suspension of sodium hydride (60% dispersion in mineral oil) in DMF (3 ml) was added a solution of 1-(2-chloro-5-thiazolylmethyl)-3,3-dimethyl-2-nitroguanidine (0.49 g) in DMF (3 ml) dropwise over 5 minutes at room temperature under stirring. After stirring for five minutes, 2.08M solution of cyanogen bromide in CH3CN (1 ml) was added to the mixture over 5 minutes. After stirring for 1 hour, the reaction mixture was poured into 50 ml of water and the reaction vessel was washed with 10 ml of water. The washing was combined with the aqueous layer and precipitated pellets were obtained by filtration and recrystallized from EtOH to afford 0.334 g of 1-(2-chloro-5-thiazolylmethyl)-1-cyano-3,3-dimethyl-2-nitroguanidine (Compound No. 1) as a crystal, m.p. 152°-155° C.

Workup

  1. stirringAfter stirring for five minutes
  2. stirringAfter stirring for 1 hour
  3. washthe reaction vessel was washed with 10 ml of water
  4. customprecipitated pellets
  5. customwere obtained by filtration
  6. customrecrystallized from EtOH

Sources & evidence

ORD record
ord-38b83a2b9ef94cc4b35fd1b95231eccd
Source dataset
uspto-grants-1993_10
Patent number
US05256679

Reaction notes

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