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

HRID 1611882Notes

Reaction equation

HRID 1611882 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

Procedure

A mixture of 3-fluoro-4-nitroaniline (1.56 g, 10 mmol), 1-methylpyrrolidinone (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. temperaturewas heated to 115–125° C. for 9.5 h
  2. extractionextracted with ethyl ether
  3. washThe combined extracts were washed with water
  4. washwashed with saturated brine solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe extract was concentrated

Sources & evidence

ORD record
ord-7ee521bf9d634c0d868acc221365b932
Source dataset
uspto-grants-2006_01
Patent number
US06991834B1

Reaction notes

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