2-Nitropropane → HCID 59355188, compound

HRID 1023492Notes

Reaction equation

HRID 1023492 reaction equation
[N+:1]([CH:4]([CH3:6])[CH3:5])([O-:3])=[O:2].[CH3:7][N:8]([CH3:12])[CH2:9][CH2:10][NH2:11].[OH-].[Na+].[CH2:15]=O>CC(O)C.O>[CH3:7][N:8]([CH3:12])[CH2:9][CH2:10][NH:11][CH2:5][C:4]([CH3:15])([N+:1]([O-:3])=[O:2])[CH3:6]

Participants

7

Reactant 4

HCID 3982-NitropropaneHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 66053N,N-Dimethylethylenediamine

Product 1

HCID 59355188HCID 59355188, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 3776IsopropanolSolvent

Procedure

To a solution of 2-nitropropane (2.07 g, 23.2 mmol) and N1,N1-dimethyl-ethane-1,2-diamine (2.22 g, 25.2 mmol) in 2-propanol (5 ml) was added 5 M NaOH in H2O (30 ul, 0.15 mmol), H2O (1 ml). 37% Formaldehyde in H2O (1.8 ml, 24 mmol) was added dropwise, and the reaction stirred for 22 h. The solution was concentrated in vacuo to half volume, acidified with sat. NaHSO4 to pH 2, and washed with 3× 100 ml CH2Cl2. 15% NaOH in H2O was added to pH 12, and the slurry extracted with 3× 100 ml CH2Cl2. The organic phases were combined, dried on MgSO4, concentrated in vacuo, and used without further purification. ESI/APCI (pos) expected for C8H19N3O2: 189.15. Found: 190 (MH+).

Workup

  1. concentrationThe solution was concentrated in vacuo to half volume
  2. washwashed with 3× 100 ml CH2Cl2
  3. addition15% NaOH in H2O was added to pH 12
  4. extractionthe slurry extracted with 3× 100 ml CH2Cl2
  5. customdried on MgSO4
  6. concentrationconcentrated in vacuo
  7. customused without further purification

Sources & evidence

ORD record
ord-88be1e0339e94bcaa0ac2aa683822073
Source dataset
uspto-grants-2014_05
Patent number
US08722715B2

Reaction notes

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