Dimethylformamide → HCID 13922984, compound

HRID 1494545Notes

Reaction equation

HRID 1494545 reaction equation
[CH3:1]N(C)C=O.P(Cl)(Cl)(Cl)=O.[CH3:11][O:12][C:13]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:14]=1[NH:15]/[C:16](/[CH3:23])=[CH:17]\[C:18]([O:20][CH2:21][CH3:22])=[O:19]>ClC(Cl)C>[CH3:29][O:28][C:25]1[CH:26]=[CH:27][C:13]([O:12][CH3:11])=[C:14]2[C:24]=1[CH:1]=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:16]([CH3:23])=[N:15]2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 67619752HCID 67619752, compound

Product 1

HCID 13922984HCID 13922984, compoundYield 127.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

To a 0° C. solution of dimethylformamide (7.5 mL, 0.097 mol) in dichloroethane (20 mL) is added dropwise phosphorous oxychloride (9.0 mL, 0.097 mol). After stirring for 3.5 hours at room temperature, a solution of ethyl 3-(2,5-dimethoxyanilino)crotonate (25.8 g, 0.097 mol) in dichloroethane (130 mL) is added dropwise at 25° C. The resulting solution is heated at reflux temperature for 3 hours. After cooling to room temperature, the reaction is quenched by the addition of an aqueous ammonium chloride solution. Methylene chloride (200 mL) is added and the layers are separated. The organic layer is dried over anhydrous magnesium sulfate and concentrated in vacuo to give a residue. The residue is purified by chromatography using silica gel and ethyl acetate in hexanes as eluant to yield the title compound (34 g, 100%) as a yellow solid identified by IR and NMR spectral analyses.

Workup

  1. temperatureThe resulting solution is heated
  2. temperatureat reflux temperature for 3 hours
  3. temperatureAfter cooling to room temperature
  4. customthe reaction is quenched by the addition of an aqueous ammonium chloride solution
  5. additionMethylene chloride (200 mL) is added
  6. customthe layers are separated
  7. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customto give a residue
  10. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-5fc83c2795aa453898b8b194baec7314
Source dataset
uspto-grants-1991_06
Patent number
US05026859

Reaction notes

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