Benzophenone → Methyl N-(diphenylmethylidene)glycinate

HRID 1894930Notes

Reaction equation

HRID 1894930 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:16][O:17][C:18](=[O:21])[CH2:19][NH2:20].CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[CH3:16][O:17][C:18](=[O:21])[CH2:19][N:20]=[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3102BenzophenoneHCID 81531DiisopropylethylamineHCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 563248Methyl N-(diphenylmethylidene)glycinateYield 205.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 500 mL, 1-necked rbf equipped with a magnetic stirrer, and a Dean-Stark apparatus with a nitrogen inlet was charged with benzophenone (58.0 g, 0.318 mol), glycine methyl ester hydrochloride (20 g, 0.159 mol) and toluene (100 mL). The resulting white suspension was heated to reflux and DIEA (56 mL, 0.318 mol) was added over three hours using a syringe pump. The resulting pale yellow solution was stirred at reflux for an additional 1 h. Upon reaction completion, the reaction mixture was cooled to rt. The reaction mixture was then washed with water (50 mL). The layers were separated and the organic solution was washed with water (50 mL) and concentrated in vacuo at 35-40° C. to give (Benzhydrylideneamino)-acetic acid methyl ester (82.59 g). In a similar fashion, (benzhydrylideneamino)-acetic acid ethyl ester was prepared.

Workup

  1. customA 500 mL, 1-necked rbf equipped with a magnetic stirrer
  2. temperatureThe resulting white suspension was heated
  3. temperatureto reflux
  4. temperatureat reflux for an additional 1 h
  5. customUpon reaction completion
  6. washThe reaction mixture was then washed with water (50 mL)
  7. customThe layers were separated
  8. washthe organic solution was washed with water (50 mL)
  9. concentrationconcentrated in vacuo at 35-40° C.

Sources & evidence

ORD record
ord-f4346db6fe5d4a5896e85b61c16bcff5
Source dataset
uspto-grants-2013_08
Patent number
US08513415B2

Reaction notes

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