L-Alanine → HCID 15337303, compound

HRID 840557Notes

Reaction equation

HRID 840557 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[NH2:12][C@H:13]([C:15]([OH:17])=[O:16])[CH3:14].[OH-].[Na+]>COCCO>[Cl:8][C:6]1[CH:7]=[C:2]([NH:12][C@H:13]([C:15]([OH:17])=[O:16])[CH3:14])[C:3]([N+:9]([O-:11])=[O:10])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 5950L-AlanineHCID 118992,4-DichloronitrobenzeneHCID 14798Sodium Hydroxide

Product 1

HCID 15337303HCID 15337303, compound

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

2,4-Dichloronitrobenzene (21.0 g, 0.109 mol) and 23.0 g (0.258 mol) of L-alanine were refluxed for 48 hours in 400 ml of 2-methoxyethanol with an addition of 120 ml of 2N sodium hydroxide solution. The mixture was subsequently concentrated in vacuo, and the residue was taken up in aqueous sodium hydrogen carbonate solution. The mixture was extracted three times using ethyl acetate, the extract was then acidified with 6N hydrochloric acid, and the yellow product was extracted using ethyl acetate. The organic phase was washed once with saturated aqueous sodium chloride solution and dried (magnesium sulfate), and the solvent was removed under reduced pressure. 14.7 g (55%) of a yellow solid of melting point 167-169° C. remained (after crystallization from ethyl acetate).

Workup

  1. concentrationThe mixture was subsequently concentrated in vacuo
  2. extractionThe mixture was extracted three times
  3. extractionthe yellow product was extracted
  4. washThe organic phase was washed once with saturated aqueous sodium chloride solution
  5. dry with materialdried (magnesium sulfate)
  6. customthe solvent was removed under reduced pressure
  7. custom(after crystallization from ethyl acetate)

Sources & evidence

ORD record
ord-6b5622245aef4c999897d37159147dbf
Source dataset
uspto-grants-2002_04
Patent number
US06369057B1

Reaction notes

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