Dimethylformamide → HCID 18998721, compound

HRID 2260667Notes

Reaction equation

HRID 2260667 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][N:15]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH2:19][CH2:18][C:17]2[CH:26]=[CH:27][CH:28]=[CH:29][C:16]1=2)#[N:7].CN([CH:33]=[O:34])C>>[CH:33]([C:24]1[CH:23]=[CH:22][C:21]2[N:15]([CH2:14][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[C:6]#[N:7])[C:16]3[CH:29]=[CH:28][CH:27]=[CH:26][C:17]=3[CH2:18][CH2:19][C:20]=2[CH:25]=1)=[O:34]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 18998680HCID 18998680, compound

Product 1

HCID 18998721HCID 18998721, compoundYield 75%

Conditions

Temperature
70 °C

Procedure

DMF (5 ml) was added dropwise to 5 ml of phosphorus oxychloride with cooling. To the solution was added dropwise 40 ml of a solution of 7.0 g of Compound 37-a in DMF, followed by stirring at 70° C. for 6 hours. The reaction mixture was poured onto ice, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [eluent: hexane/ethyl acetate (2/1)] to give 5.83 g (75%) of the product as a yellow amorphous solid.

Workup

  1. temperaturewith cooling
  2. additionThe reaction mixture was poured onto ice
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography [eluent: hexane/ethyl acetate (2/1)]

Sources & evidence

ORD record
ord-91e82c11129e40d29938ed9d134239a8
Source dataset
uspto-grants-1995_12
Patent number
US05478840

Reaction notes

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