Triethylamine → HCID 178501580, compound

HRID 633962Notes

Reaction equation

HRID 633962 reaction equation
C(N(CC)CC)C.Cl.[CH3:9][O:10][C:11](=[O:14])[CH2:12][NH2:13].[CH:15](=O)[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1.S([O-])([O-])(=O)=O.[Na+].[Na+]>ClCCl>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16](/[CH:15]=[N:13]/[CH2:12][C:11]([O:10][CH3:9])=[O:14])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24436Sodium SulfateHCID 312444-MethoxybenzaldehydeHCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 178501580HCID 178501580, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (4.6 mL, 33 mmol) and glycine methyl ester hydrochloride (3.8 g, 30.26 mmol) were successively added to a solution of p-anisaldehyde (2.0 g, 14.7 mmol) in dichloromethane (150 mL) at 0° C. Sodium sulfate (10 g) was added and the reaction mixture was stirred overnight at room temperature. The reaction mixture was then filtered and concentrated to dryness. The resulting residue was portioned in ethyl acetate and filtered in order to remove the triethylamine salts. The title compound was obtained as a pale yellow solid (4.43 g, 100%).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated to dryness
  3. filtrationfiltered in order
  4. customto remove the triethylamine salts

Sources & evidence

ORD record
ord-3ed4aca1a4704ae086a125845b916a0b
Source dataset
uspto-grants-2016_04
Patent number
US09321769B2

Reaction notes

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