Dimethylformamide → HCID 66643050, compound

HRID 869261Notes

Reaction equation

HRID 869261 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[O:23]1[C:27]2([CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[O:26][CH2:25][CH2:24]1>C(OCC)(=O)C>[CH3:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[N:30]1[CH2:31][CH2:32][C:27]2([O:26][CH2:25][CH2:24][O:23]2)[CH2:28][CH2:29]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-

Product 1

HCID 66643050HCID 66643050, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 1-fluoro-2-methyl-4-nitrobenzene (3.0 g), potassium carbonate (5.35 g) and DMF (30 mL), 1,4-dioxa-8-azaspiro[4.5]decane (4.15 g) was added and stirred at 80° C. for 20 hours. After cooling, the reaction liquid was diluted with ethyl acetate and washed with water and saturated aqueous sodium chloride. After drying over anhydrous magnesium sulfate, the solvent was distilled off, and the residue was purified by silica gel column chromatography (eluent; chloroform:methanol=100:0 to 100:1) to give 8-(2-methyl-4-nitrophenyl)-1,4-dioxa-8-azaspiro[4.5]decane (5.13 g) as a yellow solid.

Workup

  1. additionwas added
  2. temperatureAfter cooling
  3. customthe reaction liquid
  4. washwashed with water and saturated aqueous sodium chloride
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customthe residue was purified by silica gel column chromatography (eluent; chloroform:methanol=100:0 to 100:1)

Sources & evidence

ORD record
ord-c1b9dc2c1cdd49d4b2d509a89d21340a
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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