N,N-Dimethyl-1,3-propanediamine → HCID 62084069, compound

HRID 1532675Notes

Reaction equation

HRID 1532675 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][NH2:6].Cl[C:9]1[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17]>C1(C)C=CC=CC=1>[Cl:15][C:14]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:16]([O-:18])=[O:17])[C:9]=1[NH:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:7])[CH3:1]

Participants

4

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 185552,3-Dichloronitrobenzene

Product 1

HCID 62084069HCID 62084069, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
125 °C

Procedure

N,N-Dimethyl-1,3-propanediamine (5.125 g) was added to 2,3-dichloronitrobenzene (3.841 g) and stirred for 13.5 hours at 125° C. The reaction mixture, with toluene added thereto, was washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and concentrated. The residue (4.881 g) was purified by silica gel column chromatography (silica gel 100 g, chloroform:methanol=1:0-50:1), thereby yielding the entitled compound (4.53 g) as reddish orange oil.

Workup

  1. washwas washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively
  2. dry with materialdried over sodium sulfate anhydride
  3. concentrationconcentrated
  4. customThe residue (4.881 g) was purified by silica gel column chromatography (silica gel 100 g, chloroform:methanol=1:0-50:1)

Sources & evidence

ORD record
ord-e8f04a6ebdf440b0aa1f3ec83f8cb36f
Source dataset
uspto-grants-2001_03
Patent number
US06204264B1

Reaction notes

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