DL-alanine → HCID 2764588, compound

HRID 1758888Notes

Reaction equation

HRID 1758888 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH3:11])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH3:15][CH:16]([NH2:20])[C:17]([OH:19])=[O:18].C(=O)(O)[O-].[Na+]>C(O)C.O>[CH3:11][C:5]1[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([NH:20][CH:16]([CH3:15])[C:17]([OH:19])=[O:18])=[C:3]([N+:12]([O-:14])=[O:13])[CH:4]=1

Participants

6

Reactant 3

HCID 602DL-alanineHCID 789184-Chloro-3,5-dinitrotolueneHCID 516892Sodium Bicarbonate

Product 1

HCID 2764588HCID 2764588, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 810 g of 4-chloro-3,5-dinitrotoluene, 384 g of dl-alpha-alanine, and 840 g of sodium bicarbonate was stirred and refluxed in 8 l of 95% ethanol for 18 hours. The mixture was diluted with water, filtered, and the ethanol was distilled off under reduced pressure. 1 l of water was added during the distillation in order to maintain the solids in solution. The aqueous solution was cooled by the addition of 2 kg of ice and acidified with concentrated hydrochloric acid (Congo Red) whilst stirring. The initially formed sticky precipitate crystallized on continued stirring to a dark-yellow solid which was filtered off, washed with water, and air-dried to give 2-(4-methyl-2,6-dinitroanilino)propionic acid (1 A), m.p.: 158°-161° C.

Workup

  1. filtrationfiltered
  2. distillationthe ethanol was distilled off under reduced pressure
  3. addition1 l of water was added during the distillation in order
  4. temperatureto maintain the solids in solution
  5. temperatureThe aqueous solution was cooled by the addition of 2 kg of ice
  6. stirringwhilst stirring
  7. customThe initially formed sticky precipitate crystallized
  8. stirringon continued stirring to a dark-yellow solid which
  9. filtrationwas filtered off
  10. washwashed with water
  11. customair-dried

Sources & evidence

ORD record
ord-0bba075f198449da98781704fa09b895
Source dataset
uspto-grants-1982_07
Patent number
US04338121

Reaction notes

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