2,5-Dichloronitrobenzene → HCID 68461880, compound

HRID 1042692Notes

Reaction equation

HRID 1042692 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][N:13]([CH3:19])[CH2:14][CH2:15][CH2:16][NH:17][CH3:18]>Cl>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([N:17]([CH2:16][CH2:15][CH2:14][N:13]([CH3:19])[CH3:12])[CH3:18])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

4

Reactant 2

HCID 69772,5-DichloronitrobenzeneHCID 783021,3-Propanediamine, N1,N1,N3-trimethyl-

Product 1

HCID 68461880HCID 68461880, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 2,5-dichloronitrobenzene (3.0 g, 16 mmol) was added N1,N1,N3-trimethylpropane-1,3-diamine (2.2 g, 19 mmol). The mixture was stirred for 2.5 days at RT, diluted with 0.01 N HCl and extracted with EtOAc. The aqueous layer was made basic with Na2CO3 and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated to yield 4-chloro-N-(3-(dimethylamino)propyl)-N-methyl-2-nitrobenzenamine as an orange oil. MS m/z=272 [M+H]−. Calc'd for C12H18ClN3O2: 271.75.

Workup

  1. extractionextracted with EtOAc
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-32072b2fb9504d2c90d241536090d696
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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