Dimethylformamide → HCID 21714329, compound

HRID 1600620Notes

Reaction equation

HRID 1600620 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH3:7][N:8]([C:18]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:19]=1[N+:28]([O-:30])=[O:29])[CH2:9][CH2:10][O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1.[I-].C[S+](C)C.CN(C)C=O>O1CCCC1.O>[CH3:1][C:20]1[C:19]([N+:28]([O-:30])=[O:29])=[C:18]([N:8]([CH3:7])[CH2:9][CH2:10][O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[CH:23]=[CH:22][C:21]=1[C:24]([F:26])([F:27])[F:25]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 75127Trimethylsulfonium iodideHCID 21714364HCID 21714364, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21714329HCID 21714329, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
17.5 °C

Procedure

A solution of potassium tert-butoxide (3.22 g, 28.7 mmol) in tetrahydrofuran (40 ml) was added dropwise to a mixture of 4-[N-methyl-N-[2-(2-tetrahydro-2H-pyranyl)oxyethyl]amino]-3-nitrobenzotrifluoride (5.00 g, 14.4 mmol), trimethylsulfonium iodide (5.86 g, 28.7 mmol) and N,N-dimethylformamide (80 ml) with stirring at 15-20° C. After stirring at 15-16° C. for another 1 hour, the reaction mixture was cooled to 0° C. The reaction mixture was poured into cold water and extracted three times with ethyl acetate. The extract solution was washed twice with a 5% aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=3/97) to obtain an oil of 2-methyl-4-[N-methyl-N-[2-(2-tetrahydro-2H-pyranyl)oxyethyl]amino]-3-nitrobenzotrifluoride.

Workup

  1. stirringAfter stirring at 15-16° C. for another 1 hour
  2. temperaturethe reaction mixture was cooled to 0° C
  3. extractionextracted three times with ethyl acetate
  4. washThe extract solution was washed twice with a 5% aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=3/97)

Sources & evidence

ORD record
ord-e212892bd16e487a8067998fc408c783
Source dataset
uspto-grants-1999_11
Patent number
US05977100

Reaction notes

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