Benzaldehyde → Methyl 2-phenyl-2-[(phenylmethylene)amino]acetate

HRID 507436Notes

Reaction equation

HRID 507436 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:13])[CH:5]([NH2:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.[CH:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[O-]S([O-])(=O)=O.[Mg+2]>ClCCl>[CH3:2][O:3][C:4](=[O:13])[CH:5]([N:12]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 12247454Methyl 2-amino-2-phenylacetate hydrochloride

Product 1

HCID 3714052Methyl 2-phenyl-2-[(phenylmethylene)amino]acetateYield 96.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8 (40.3 g, 0.2 mol) in dichloromethane (600 mL) was added triethyl amine (24.24 g, 0.24 mol) dropwise. After stirring for 30 min, benzaldehyde (21.2 g, 0.2 mol) was added dropwise, followed by the addition of MgSO4 (240 g, 2 mol). The mixture was stirred overnight. After filtration, the filtrate was evaporated to give compound 9 (49 g, 96.8%). 1H NMR (400 MHz, CDCl3) δ 3.72 (s, 3 H), 5.22 (s, 1 H), 7.30-7.39 (m, 6 H), 7.53-7.56 (m, 2 H), 7.82-7.85 (m, 2 H), 8.34 (s, 1 H).

Workup

  1. stirringThe mixture was stirred overnight
  2. filtrationAfter filtration
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-52e801dd110043ddb5e7bbd0ebaead9c
Source dataset
uspto-grants-2010_08
Patent number
US07786163B2

Reaction notes

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