2,3,6-Trichlorobenzoic acid → (Aminocarbonyl)Methyl 2,3,6-Trichlorobenzoate

HRID 1105716

Reaction equation

HRID 1105716 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[C:7]([Cl:12])[C:3]=1[C:4]([OH:6])=[O:5].[OH-].[K+].Cl[CH2:16][C:17]([NH2:19])=[O:18].O1CCOCCOCCOCCOCCOCC1>C1(C)C=CC=CC=1.CN(C)C=O>[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[C:7]([Cl:12])[C:3]=1[C:4]([O:6][CH2:16][C:17]([NH2:19])=[O:18])=[O:5]

Participants

7

Reactant 4

HCID 57592,3,6-Trichlorobenzoic acidHCID 6580ChloroacetamideHCID 14797Potassium HydroxideHCID 2855718-Crown-6

Product 1

HCID 2417794(Aminocarbonyl)Methyl 2,3,6-Trichlorobenzoate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

This compound was prepared in the manner of Example I, using 15.0 grams (0.066 mole) of 2,3,6-trichlorobenzoic acid, 4.4 grams (0.066 mole) of potassium hydroxide, 6.2 grams (0.066 mole) of 2-chloroacetamide, and 1.8 grams of 1,4,7,10,13,16-hexaoxacyclooctadecane in 300 ml of dry toluene and 200 ml of dimethylformamide. The crude product was purified by liquid chromatography, followed by recrystallization from ethyl acetate. The yield was 0.9 gram of (aminocarbonyl)methyl 2,3,6-trichlorobenzoate; mp 158°-160°. The ir and the nmr spectra were consistent with the proposed structure.

Workup

  1. customThis compound was prepared in the manner of Example I
  2. customThe crude product was purified by liquid chromatography
  3. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-f67ddac55063423aa6c6229eb1daa2d8
Source dataset
uspto-grants-1982_01
Patent number
US04309566

Linked notes

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