Potassium Carbonate → N,N-diallyl-6-nitro-1,3-benzenediamine

HRID 1871176Notes

Reaction equation

HRID 1871176 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10])[NH2:5].CN1CCCC1=O.[CH2:19]([NH:22][CH2:23][CH:24]=[CH2:25])[CH:20]=[CH2:21].C(=O)([O-])[O-].[K+].[K+]>O>[CH2:19]([N:22]([CH2:23][CH:24]=[CH2:25])[C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[C:4]([NH2:5])[CH:3]=1)[CH:20]=[CH2:21]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 31279DiallylamineHCID 754013-Fluoro-4-nitroaniline

Product 1

HCID 22251449N,N-diallyl-6-nitro-1,3-benzenediamineYield 98.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-fluoro-4-nitroaniline (1.56 g, 10 mmol), 1-methylpyrolidinone (10 mL), diallylamine (1.94 g, 20 mmol) and potassium carbonate (1.38 g, 10 mmol) was heated to 115-125° C. for 9.5 h. The mixture was diluted with water, and extracted with ethyl ether. The combined extracts were washed with water, washed with saturated brine solution, and dried over magnesium sulfate. The extract was concentrated to give N,N-diallyl-6-nitro-1,3-benzenediamine as an orange oil (2.3 g).

Workup

  1. extractionextracted with ethyl ether
  2. washThe combined extracts were washed with water
  3. washwashed with saturated brine solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe extract was concentrated

Sources & evidence

ORD record
ord-fb85b477804744acb97849ae2beaad03
Source dataset
uspto-grants-2000_08
Patent number
US06103322

Reaction notes

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