Carbon Dioxide → Methyl N-(2,6-dimethylphenyl)-DL-alaninate

HRID 258725

Reaction equation

HRID 258725 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].C([O-])(O)=O.[Na+].[CH3:15][O:16][C:17](=[O:21])[CH:18](Br)[CH3:19].C(=O)=O>>[CH3:15][O:16][C:17](=[O:21])[CH:18]([NH:4][C:3]1[C:5]([CH3:9])=[CH:6][CH:7]=[CH:8][C:2]=1[CH3:1])[CH3:19]

Participants

5

Reactant 4

HCID 280Carbon DioxideHCID 68962,6-DimethylanilineHCID 95576Methyl 2-bromopropionateHCID 516892Sodium Bicarbonate

Product 1

HCID 94555Methyl N-(2,6-dimethylphenyl)-DL-alaninate

Procedure

6 g-moles of 2,6-dimethylaniline, 6.6 g-moles of NaHCO3 and 18.0 g-moles of α-bromopropionic acid methyl ester are placed together and heated slowly, with stirring, for 1 hour upto 120°-125° C. bath temperature. As CO2 is evolved, stirring of the mixture at this temperature is continued for 18 hours. The mixture is subsequently cooled, the inorganic constituents are filtered off, and the filtrate distilled in a water-jet vacuum (ca. 10- 12 Torr). After removal of the excess α-bromopropionic acid methyl ester, the resulting yield is 990.3 g (79.6% of theory) of final product, which boils at 133°-134° (12 Torr).

Workup

  1. temperatureheated slowly
  2. stirringstirring of the mixture at this temperature
  3. waitis continued for 18 hours
  4. temperatureThe mixture is subsequently cooled
  5. filtrationthe inorganic constituents are filtered off
  6. distillationthe filtrate distilled in a water-jet vacuum (ca. 10- 12 Torr)
  7. customAfter removal of the excess α-bromopropionic acid methyl ester

Sources & evidence

ORD record
ord-c195497bba66413cbd93778b6c8f84f3
Source dataset
uspto-grants-1977_07
Patent number
US04034108

Linked notes

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