Methanol → N-(2-chloro-5-thiazolylmethyl)-N'-methyl-N"-nitroguanidine

HRID 1069386Notes

Reaction equation

HRID 1069386 reaction equation
[Cl:1][C:2]1[S:3][C:4]([CH2:7][N:8]2CN(C)[CH2:11][N:10](C)[C:9]2=[N:16][N+:17]([O-:19])=[O:18])=[CH:5][N:6]=1.C([O-])(O)=O.[Na+].CO.O>C(OCC)(=O)C>[Cl:1][C:2]1[S:3][C:4]([CH2:7][NH:8][C:9]([NH:10][CH3:11])=[N:16][N+:17]([O-:19])=[O:18])=[CH:5][N:6]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 516892Sodium BicarbonateHCID 541268941-(2-Chloro-5-thiazolylmethyl)-3,5-dimethyl-2-nitroiminohexahydro-1,3,5-triazine

Product 1

HCID 135779804N-(2-chloro-5-thiazolylmethyl)-N'-methyl-N"-nitroguanidine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1.5 g of 1-(2-chlorothiazol-5-ylmethyl)-2-nitroimino-3,5-dimethyl-1,3,5-triaza-cyclohexane, 0.3 g of NaHCO3, 20 ml of methanol and 20 ml of water is stirred for 16 hours at 50° C. The reaction mixture is poured onto 100 ml of ethyl acetate and the aqueous phase separated. The organic phase is concentrated by evaporation and the residue purified on silica gel with dichloromethane/methanol 95:5 as the eluant. This yields the title compound with a melting point of 167-169° C. (compound 2.45).

Workup

  1. customthe aqueous phase separated
  2. concentrationThe organic phase is concentrated by evaporation
  3. customthe residue purified on silica gel with dichloromethane/methanol 95:5 as the eluant

Sources & evidence

ORD record
ord-0144165d2a6b446487ddbf75bdce8043
Source dataset
uspto-grants-2001_06
Patent number
US06252072B1

Reaction notes

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