Dimethylamine → HCID 21206582, compound

HRID 1052617Notes

Reaction equation

HRID 1052617 reaction equation
F[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([I:11])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:18][NH:19][CH3:20].O>CS(C)=O>[I:11][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=1)[N:19]([CH3:20])[CH3:18]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 11430Potassium CarbonateHCID 2590861-Fluoro-3-iodo-5-nitrobenzene

Product 1

HCID 21206582HCID 21206582, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
125 °C

Procedure

1-Fluoro-3-iodo-5-nitrobenzene (500 mg, 1.87 mmol), and potassium carbonate (260 mg, 1.88 mmol) were suspended in DMSO (7 ml) and dimethylamine (2M in THF, 3 ml, 6 mmol) was added. The vial was sealed under argon and stirred for 15 min at 125° C. under microwave conditions. The reaction mixture was poured into 50 ml of water and extracted with ethyl acetate (3×40 ml). The organic phase was washed with brine (1×100 ml), dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified using SP1® Purification System (0% to 30%, hexane-ethyl acetate) to obtain 320 mg (59% yield) of the title compound as a brown solid. Purity 100%.

Workup

  1. customThe vial was sealed under argon
  2. extractionextracted with ethyl acetate (3×40 ml)
  3. washThe organic phase was washed with brine (1×100 ml)
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified
  7. customSP1® Purification System (0% to 30%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-85e8085c64154f4589b41afd76b5d735
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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