Ethanol → 1-Benzyl-1-methyl-3-nitroguanidine

HRID 2166305Notes

Reaction equation

HRID 2166305 reaction equation
CNC[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:10][N:11](N=O)/[C:12](/[NH2:17])=[N:13]/[N+:14]([O-:16])=[O:15].[CH2:20](O)C>>[CH2:10]([N:11]([CH3:20])[C:12]([NH:13][N+:14]([O-:16])=[O:15])=[NH:17])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 7669N-MethylbenzylamineHCID 95620601-Methyl-2-nitro-1-nitrosoguanidine

Product 1

HCID 1356162101-Benzyl-1-methyl-3-nitroguanidine

Procedure

N-Methylbenzylamine (9.89 g, 0.082 mol) is added dropwise to a suspension of MNNG (10.0 g, 0.068 mol) in aqueous ethanol (1:1 ethanol:water, v/v) at 25° C. A gradual exotherm to 44° C. occurs over the next 15 minutes. After stirring for 42 hours at ambient temperature, the white slurry is filtered. The resultant white solid (7.13 g) is recrystallized from hexanes:ethanol to afford pure product (white crystals, 6.06 g, 43.0%, melting point 103° C. -107° C.).

Workup

  1. customto 44° C.
  2. customoccurs over the next 15 minutes
  3. filtrationthe white slurry is filtered
  4. customThe resultant white solid (7.13 g) is recrystallized from hexanes
  5. customethanol to afford pure product (white crystals, 6.06 g, 43.0%, melting point 103° C. -107° C.)

Sources & evidence

ORD record
ord-c8ed7c0cad7e49b7ab50f1b0daef9fec
Source dataset
uspto-grants-1990_07
Patent number
US04944788

Reaction notes

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