Benzoyl chloride → HCID 23093472, compound

HRID 1022299Notes

Reaction equation

HRID 1022299 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].C(OCC)(=O)C.[C:12]([Cl:20])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>N1C=CC=CC=1>[ClH:20].[C:12]([O:5][CH2:4][CH2:3][NH:2][CH3:1])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 80162-(Methylamino)ethanolHCID 8857Ethyl Acetate2×

Product 1

HCID 23093472HCID 23093472, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 2-(methylamino)ethanol (30.04 g) and ethyl acetate (90 mL) was dropwise added a mixture of di-tert-butyl Bicarbonate (87.30 g) and ethyl acetate (10 mL) under ice-cooling. After stirring at room temperature for 1 hr., benzoyl chloride (61.8 g) and pyridine (38.8 mL) were added under ice-cooling. After stirring at room temperature for 1 hr., a solid was filtered off. The solid was washed with ethyl acetate (100 mL) and the filtrate and the washing were combined, which was washed with water (100 mL) and saturated brine (100 mL). After drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (100 mL), a 4N hydrogen chloride-ethyl acetate solution (200 mL) was added, and the mixture was stirred at room temperature for 30 min. Diethyl ether (100 mL) was added and a solid was collected by filtration. The solid was washed twice with ethyl acetate (100 mL) and dried under reduced pressure at 60° C. to give the title compound (57.4 g) as a white solid.

Workup

  1. additionwas dropwise added
  2. temperaturecooling
  3. temperaturecooling
  4. stirringAfter stirring at room temperature for 1 hr
  5. filtration, a solid was filtered off
  6. washThe solid was washed with ethyl acetate (100 mL)
  7. washwhich was washed with water (100 mL) and saturated brine (100 mL)
  8. dry with materialAfter drying over anhydrous magnesium sulfate
  9. concentrationthe mixture was concentrated under reduced pressure
  10. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
  11. additiona 4N hydrogen chloride-ethyl acetate solution (200 mL) was added
  12. stirringthe mixture was stirred at room temperature for 30 min
  13. additionDiethyl ether (100 mL) was added
  14. filtrationa solid was collected by filtration
  15. washThe solid was washed twice with ethyl acetate (100 mL)
  16. customdried under reduced pressure at 60° C.

Sources & evidence

ORD record
ord-ca12b902ca20436fa98434c889eb1cc0
Source dataset
uspto-grants-2014_05
Patent number
US08722084B2

Reaction notes

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