2-Nitropropane → N-(2-methyl-2-nitropropyl)-4,4-dimethyl-1,3-oxazolidine

HRID 371912Notes

Reaction equation

HRID 371912 reaction equation
[N+:1]([CH:4]([CH3:6])[CH3:5])([O-:3])=[O:2].[CH2:7]=O.[CH3:9][C:10]1([CH3:15])[NH:14][CH2:13][O:12][CH2:11]1>>[CH3:5][C:4]([N+:1]([O-:3])=[O:2])([CH3:7])[CH2:6][N:14]1[C:10]([CH3:15])([CH3:9])[CH2:11][O:12][CH2:13]1

Participants

4

Reactant 3

HCID 3982-NitropropaneHCID 712FormaldehydeHCID 620104,4-Dimethyl oxazolidine

Product 1

HCID 20352304N-(2-methyl-2-nitropropyl)-4,4-dimethyl-1,3-oxazolidine

Conditions

Temperature
65 °C

Procedure

2-Nitropropane 89 g (1 mole) and 37% formaldehyde 88 g (1 mole) were mixed together and heated to 65° C. There was then added dropwise Oxazolidine A 101 g (1 mole) and after the addition was complete, heating of the reaction mixture at 60°-70° C was continued for 2 hours. Water was then removed by distillation at about 8-12 mm Hg pressure. There was obtained N-(2-methyl-2-nitropropyl)-4,4-dimethyl-1,3-oxazolidine. It analyzed carbon 53.65% (calc. 53.47), hydrogen 9.07% (calc. 8.98) and nitrogen 13.47% (calc. 13.87). The compound was effective against bacteria and fungi at a concentration of 500 μg/ml or less as shown in Table 1.

Workup

  1. additionafter the addition
  2. temperatureheating of the reaction mixture at 60°-70° C
  3. customWater was then removed by distillation at about 8-12 mm Hg pressure

Sources & evidence

ORD record
ord-51f7f7870d384a268ac412971a92328d
Source dataset
uspto-grants-1978_05
Patent number
US04088655

Reaction notes

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