Dichloromethane → Methyl (2E)-[(diphenylmethyl)imino]acetate

HRID 2190963Notes

Reaction equation

HRID 2190963 reaction equation
[CH:1]([NH2:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][O:16][CH:17]([OH:22])[C:18](OC)=O.[CH2:23](Cl)Cl>>[CH:17]([O:22][CH:13]([CH3:12])[CH3:8])([CH3:23])[CH3:18].[CH3:9][CH2:8][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5].[CH:1]([N:14]=[CH:18][C:17]([O:16][CH3:15])=[O:22])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7036BenzhydrylamineHCID 2724791Methyl 2-Hydroxy-2-methoxyacetate

Product 2

HCID 12624354Methyl (2E)-[(diphenylmethyl)imino]acetateYield 79%HCID 22997467HCID 22997467, compound

Procedure

Benzhydrylamine (48.8 g, 0.266 mol) was added drop wise to a solution of glyoxylic acid methyl ester methyl hemiacetal (32 g, 0.266 mol) in methylene chloride (300 mL). The mixture was stirred for 3 hours at room temperature and then dried over magnesium sulfate. The mixture was filtered and the solvent was removed from the filtrate under reduced pressure to yield a viscous oil. Trituration with diisopropyl ether/heptane gave methyl 2-(benzhydrylimino)acetate (53.4 g, 79%) as an off white solid. 1H-NMR (400 MHz, CDCl3): δ=3.82 (s, 3H), 7.17-7.31 (m, 10H), 7.73 (s, 1H).

Workup

  1. dry with materialdried over magnesium sulfate
  2. filtrationThe mixture was filtered
  3. customthe solvent was removed from the filtrate under reduced pressure
  4. customto yield a viscous oil

Sources & evidence

ORD record
ord-f49dddf227894a1cafc5f3a2cb3f307f
Source dataset
uspto-grants-2012_12
Patent number
US08324417B2

Reaction notes

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