Hexamethylphosphoramide → HCID 18407196, compound

HRID 2271214Notes

Reaction equation

HRID 2271214 reaction equation
[C:1]([N:4]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]([OH:27])=O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:3])[CH3:2].S(Cl)(Cl)=O.[CH3:32][N:33]([CH3:42])P(N(C)C)(N(C)C)=O>O1CCCC1>[C:1]([N:4]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]([N:33]([CH3:42])[CH3:32])=[O:27])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 12679HexamethylphosphoramideHCID 24386Thionyl ChlorideHCID 18407219HCID 18407219, compound

Product 1

HCID 18407196HCID 18407196, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a mixture of 10 ml of tetrahydrofuran and 0.1 ml of hexamethylphosphoramide was dissolved 0.50 g of N-acetyl-N-(2-carboxybenzyl)-2-phenoxyaniline, and 0.2 ml of thionyl chloride was added, followed by stirring at room temperature for 3 hours. The reaction mixture was concentrated, the residue was dissolved in 10 ml of tetrahydrofuran, and 2 ml of 50% aqueous dimethylamine solution was added dropwise with stirring. The reaction mixture was poured into water and extracted with ethyl acetate, and the extract was washed with 1 N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate-hexane=1:3) to give 0.49 g of N-acetyl-N-(2-dimethylaminocarbonylbenzyl)-2-phenoxyaniline as an oil.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in 10 ml of tetrahydrofuran
  4. addition2 ml of 50% aqueous dimethylamine solution was added dropwise
  5. stirringwith stirring
  6. additionThe reaction mixture was poured into water
  7. extractionextracted with ethyl acetate
  8. washthe extract was washed with 1 N hydrochloric acid
  9. dry with materiala saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate
  10. customAfter removal of the drying agent
  11. filtrationby filtration
  12. concentrationthe solvent was concentrated under reduced pressure
  13. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate-hexane=1:3)

Sources & evidence

ORD record
ord-790e6654dea04040808d6baeb0503cab
Source dataset
uspto-grants-2001_12
Patent number
US06333358B1

Reaction notes

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