p-Fluoronitrobenzene → HCID 86681775, compound

HRID 710599

Reaction equation

HRID 710599 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]([CH3:20])[CH:13]1[CH2:18][CH2:17][CH:16]([NH2:19])[CH2:15][CH2:14]1.C(N(C(C)C)C(C)C)C>CS(C)=O.C(OCC)(=O)C>[CH3:11][N:12]([CH3:20])[CH:13]1[CH2:18][CH2:17][CH:16]([NH:19][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:15][CH2:14]1

Participants

6

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 81531DiisopropylethylamineHCID 345823N,N-Dimethyl-1,4-cyclohexanediamine

Product 1

HCID 86681775HCID 86681775, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-fluoro-4-nitrobenzene (0.392 ml, 3.69 mmol) in 4 mL of dimethyl sulfoxide was added N1,N1-dimethylcyclohexane-1,4-diamine (500 mg, 3.52 mmol) and N-ethyl-N-isopropylpropan-2-amine (2.449 ml, 14.06 mmol). The reaction mixture was stirred at 100° C. for 24 hours. The mixture was poured into a separatory funnel and was diluted with 50 mL of ethyl acetate. The organic mixture was then washed with 50 mL of water followed by 50 mL of saturated aqueous brine. The organic phase was dried over sodium sulfate, filtered and concentrated. The crude material obtained was carried through the next step without purification. MS (ESI) m/z 264.1 (M+H)+.

Workup

  1. additionThe mixture was poured into a separatory funnel
  2. washThe organic mixture was then washed with 50 mL of water
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-81b1736b12654061a6b28cc9c4969376
Source dataset
uspto-grants-2015_11
Patent number
US09181239B2

Linked notes

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