Methanol → Methyl Bis-(2,2-dinitropropyl)-glycine

HRID 745133

Reaction equation

HRID 745133 reaction equation
[N+:1]([C:4]([N+:21]([O-:23])=[O:22])([CH3:20])[CH2:5][N:6]([CH2:11][C:12]([N+:17]([O-:19])=[O:18])([N+:14]([O-:16])=[O:15])[CH3:13])[CH2:7][C:8]([OH:10])=[O:9])([O-:3])=[O:2].S(=O)(=O)(O)O.[CH3:29]O>>[CH3:29][CH:7]([C:8]([OH:10])=[O:9])[N:6]([CH2:11][C:12]([N+:14]([O-:16])=[O:15])([N+:17]([O-:19])=[O:18])[CH3:13])[CH2:5][C:4]([N+:21]([O-:23])=[O:22])([N+:1]([O-:3])=[O:2])[CH3:20]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 54517463Bis-(2,2-dinitropropyl)-glycine

Product 1

HCID 86740873Methyl Bis-(2,2-dinitropropyl)-glycine

Procedure

A mixture of 20 g. (0.059 mole) of bis-(2,2-dinitropropyl)-glycine, 100 ml. of methanol and 10.0 ml. of concentrated sulfuric acid was refluxed for 90 minutes. The solution was diluted with 250 ml. of methylene chloride and washed with water, 5% sodium carbonate solution and water. The solvent was evaporated to yield 14.0 g. (67.3%) of white solid. Recrystallization from methanol-ether gave crystals, m.p. 94°-95°.

Workup

  1. additionA mixture of 20 g
  2. additionThe solution was diluted with 250 ml
  3. washof methylene chloride and washed with water, 5% sodium carbonate solution and water
  4. customThe solvent was evaporated
  5. customto yield 14.0 g
  6. customRecrystallization from methanol-ether
  7. customgave crystals, m.p. 94°-95°

Sources & evidence

ORD record
ord-84115ad8593443a7a29f7d5d18ef5270
Source dataset
uspto-grants-1986_07
Patent number
USH0000078

Linked notes

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