Acetylglycine → HCID 54316039, compound

HRID 1432891Notes

Reaction equation

HRID 1432891 reaction equation
[Cl:1][C:2]1[S:6][C:5]([CH:7]=O)=[CH:4][CH:3]=1.[C:9]([NH:12][CH2:13][C:14]([OH:16])=[O:15])(=O)[CH3:10].CC([O-])=O.[Na+]>CC(OC(C)=O)=O.[OH-].[Na+].C(Cl)Cl>[Cl:1][C:2]1[S:6][C:5]([CH:7]=[C:13]2[C:14](=[O:15])[O:16][C:9]([CH3:10])=[N:12]2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 10972AcetylglycineHCID 817002-Thiophenecarboxaldehyde, 5-chloro-HCID 517045Sodium Acetate

Product 1

HCID 54316039HCID 54316039, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 7918Acetic AnhydrideSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture consisting of 5-chlorothiophene-2-carboxaldehyde (1.00 g, 6.82 mmol), N-acetylglycine (0.96 g, 8.18 mmol), NaOAc (0.67 g, 8.18 mmol) in Ac2O (5 mL) is warmed at reflux for 16 hours. The reaction mixture is cooled to ambient temperature and diluted with dilute aqueous NaOH (0.5 M, 100 mL) and CH2Cl2 (100 mL). The layers are separated and the organic phase is washed with aqueous NaHCO3, brine, dried over anhydrous Na2SO4, filtered and concentrated to provide 1.5 g (100%) of the title compound as a colorless oil which is used without further purification in the next reaction. 1H NMR (300 MHz, CDCl3) δ2.39 (s, 3H), 6.94 (d, J=4.0 Hz, 1H), 7.21 (s, 1H), 7.26 (d, J=4.0 Hz, 1H) ppm.

Workup

  1. temperatureis warmed
  2. temperatureat reflux for 16 hours
  3. customThe layers are separated
  4. washthe organic phase is washed with aqueous NaHCO3, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-da6c9100ec0446b181cb1583437fc61e
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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