Hydrochloric Acid → Ethyl N-(2,3-dichloro-6-nitrobenzyl)glycine

HRID 481140Notes

Reaction equation

HRID 481140 reaction equation
Cl.C([O:4][C:5](=[O:8])[CH2:6][NH2:7])C.[Cl:9][C:10]1[C:17]([Cl:18])=[CH:16][CH:15]=[C:14]([N+:19]([O-:21])=[O:20])[C:11]=1[CH2:12]Cl.[Na+].[Cl-].Cl.[CH:25](O)(C)[CH3:26]>[Br-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.C1(C)C=CC=CC=1.C(N(CC)CC)C>[CH2:25]([N:7]([CH2:12][C:11]1[C:14]([N+:19]([O-:21])=[O:20])=[CH:15][CH:16]=[C:17]([Cl:18])[C:10]=1[Cl:9])[CH2:6][C:5]([OH:4])=[O:8])[CH3:26]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 5234Sodium ChlorideHCID 2723640Glycine ethyl ester, hydrochlorideHCID 98346632,3-Dichloro-6-nitrobenzyl chloride2×

Product 1

HCID 22439334Ethyl N-(2,3-dichloro-6-nitrobenzyl)glycineYield 66%

Reagents, catalysts & solvents 3

HCID 5974Hexadecyltrimethylammonium BromideCatalystHCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

Under nitrogen, 47.5 mL of triethylamine, 25.9 g of glycine ethyl ester hydrochloride and 2.8 g of cetyltrimethylammonium bromide is added to the toluene solution of 1,2-dichloro-3-chloromethyl-4-nitrobenzene (compound VIII) prepared in the previous step. The reaction mixture is heated at 80° C. for 24 hours. To the cooled mixture is added 40 mL of 20% NaCl solution. The organic phase is separated, washed with water, and concentrated. The salt (compound VI) is prepared in 66 to 71% yield by treating the crude material with HCl in isopropanol and filtering the precipitate.

Workup

  1. customprepared in the previous step
  2. customThe organic phase is separated
  3. washwashed with water
  4. concentrationconcentrated
  5. filtrationfiltering the precipitate

Sources & evidence

ORD record
ord-04940defef02413d83c941e83449c401
Source dataset
uspto-grants-2003_11
Patent number
US06653500B2

Reaction notes

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