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

HRID 1981841Notes

Reaction equation

HRID 1981841 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 aqueoos 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-7fe188fda6c447819ea02e096c7e3696
Source dataset
uspto-grants-1986_06
Patent number
US04594092

Reaction notes

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