Water → HCID 53849939, compound

HRID 277300Notes

Reaction equation

HRID 277300 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[C:10]([NH:13][CH2:14][C:15]([OH:17])=[O:16])(=[O:12])[CH3:11].[C:18]([O-])(=O)C.[Na+].O>C(OC(=O)C)(=O)C.CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[C:14]([NH:13][C:10](=[O:12])[CH3:11])[C:15]([O:17][CH3:18])=[O:16]

Participants

7

Reactant 4

HCID 962WaterHCID 10972AcetylglycineHCID 765833-BromobenzaldehydeHCID 517045Sodium Acetate

Product 1

HCID 53849939HCID 53849939, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 7918Acetic AnhydrideSolvent

Procedure

3-Bromobenzaldehyde (23.7 g, 128.2 mmol), N-acetyl glycine (10.0 g, 85.5 mmol) and sodium acetate (5.26 g, 64.1 mmol) in acetic anhydride (60 mL) was heated to reflux for 1 h. The reaction was cooled to room temperature and water (100 mL) was added. The resulting suspension was filtered and the solid was washed with water (2×50 mL). The remaining solid was dissolved in methylene chloride (100 mL), dried (MgSO4), filtered and concentrated in vacuo to give a yellow solid. The solid was suspended in dry MeOH (200 mL) and heated to reflux for 9 h. The reaction mixture was concentrated in vacuo to give a yellow solid. Recrystallization from EtOAc and petroleum ether gave methyl m-bromo-α-acetamidocinnamate as a yellow solid. MS (CI) m/z 298 (M++1 (Br=79), 100%), 300 (M++1 (Br=81), 100%). 13C NMR (50 MHz, d6-DMSO): δ23.3, 52.8, 122.5, 125.0, 128.06, 130.0, 130.2, 132.2, 132.3, 135.9, 165.4 and 168.8.

Workup

  1. temperatureto reflux for 1 h
  2. filtrationThe resulting suspension was filtered
  3. washthe solid was washed with water (2×50 mL)
  4. dissolutionThe remaining solid was dissolved in methylene chloride (100 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a yellow solid
  9. temperatureheated
  10. temperatureto reflux for 9 h
  11. concentrationThe reaction mixture was concentrated in vacuo
  12. customto give a yellow solid
  13. customRecrystallization from EtOAc and petroleum ether

Sources & evidence

ORD record
ord-b84f779338ba4d4596a183b3b9915c36
Source dataset
uspto-grants-2002_03
Patent number
US06355683B1

Reaction notes

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