Formaldehyde → HCID 13539132, compound

HRID 256882Notes

Reaction equation

HRID 256882 reaction equation
[NH:1]([CH2:3][C:4](O)=O)[CH3:2].[CH3:7][O:8][C:9](=[O:12])[CH:10]=[CH2:11].C=O>C1(C)C=CC=CC=1>[CH3:2][N:1]1[CH2:3][CH2:4][CH:10]([C:9]([O:8][CH3:7])=[O:12])[CH2:11]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 1088SarcosineHCID 7294Methyl Acrylate

Product 1

HCID 13539132HCID 13539132, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of sarcosine (30 g, 0.34 mol), methylacrylate (29 g, 0.34 mol) and paraformaldehyde (20.2 g, 0.67 mol) in toluene (3 l) was refluxed in a Dean-Stark trap apparatus for 0.5 h. The reaction mixture was cooled to room temperature and stirred for 16 h. Filtration through cotton wool and concentration under vacuum gave the title ester as a pale yellow liquid (21 g) m/e 143 (M+); δ(250 MHz, CDCl3) 2.05-2.16 (2H, m, CH2); 2.36 (3H, s, N--Me); 2.48-2.84 (4H, m, 2 of CH2 --N); 2.98-3.10 (1H, m, CH--CO2Me); 3.70 (3H, s, CO2Me).

Workup

  1. filtrationFiltration
  2. concentrationthrough cotton wool and concentration under vacuum

Sources & evidence

ORD record
ord-7b367fe184184637a1e6aeb212965edd
Source dataset
uspto-grants-1993_11
Patent number
US05260293

Reaction notes

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