p-Fluoronitrobenzene → HCID 22569398, compound

HRID 1110332Notes

Reaction equation

HRID 1110332 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][N:12]([CH3:16])[CH2:13][CH2:14][NH2:15].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:11][N:12]([CH3:16])[CH2:13][CH2:14][NH:15][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 66053N,N-Dimethylethylenediamine

Product 1

HCID 22569398HCID 22569398, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of 4-fluoronitrobenzene (7 g, 50 mmol), N,N-dimethylethylenediamine (5.2 g, 60 mmol) and potassium carbonate (7 g, 50 mmol) in 25 ml of dimethysulfoxide was added 0.2 g of tris(3,6-dioxaheptyl) amine(TDA-1). The heterogenous mixture was heated at 90° for 2 h. After cooling to room temperature, 100 g of crushed ice was added to precipitate out the yellow product in 90% yield (9.4 g, 45 mmol).

Workup

  1. temperatureThe heterogenous mixture was heated at 90° for 2 h
  2. customto precipitate out the yellow product in 90% yield (9.4 g, 45 mmol)

Sources & evidence

ORD record
ord-cc816448f022489481868fbb30556924
Source dataset
uspto-grants-1990_12
Patent number
US04975092

Reaction notes

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