2,6-Dichlorobenzoic acid → HCID 86738201, compound

HRID 1105718Notes

Reaction equation

HRID 1105718 reaction equation
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([OH:6])=[O:5].[OH-].[K+].[CH3:14][N:15]([CH3:21])[NH:16][C:17](=[O:20])[CH2:18][Cl:19].O1CCOCCOCCOCCOCCOCC1>C1(C)C=CC=CC=1>[CH3:14][N:15]([CH3:21])[NH:16][C:17](=[O:20])[CH:18]([O:6][C:4](=[O:5])[C:3]1[C:7]([Cl:11])=[CH:8][CH:9]=[CH:10][CH:2]=1)[Cl:19]

Participants

6

Reactant 4

HCID 57582,6-Dichlorobenzoic acidHCID 14797Potassium HydroxideHCID 2855718-Crown-6HCID 125593462-Chloroacetic acid 2,2-dimethylhydrazide

Product 1

HCID 86738201HCID 86738201, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

This compound was prepared in the manner of Example I, using 12.2 grams (0.064 mole) of 2,6-dichlorobenzoic acid, 4.2 grams (0.064 mole) of potassium hydroxide, 8.7 grams (0.064 mole) of chloroacetic acid 2,2-dimethylhydrazide, and 1.7 grams of 1,4,7,10,13,16-hexaoxacyclooctadecane in 180 ml of dry toluene. The crude product was recrystallized twice from ethyl acetate using decolorizing carbon to give 18.6 grams of 2,6-dichlorobenzoyloxyacetic acid 2,2-dimethylhydrazide; mp 160°-162°. 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 recrystallized twice from ethyl acetate using

Sources & evidence

ORD record
ord-a4f08cbf7fb342f1b3ebe60301956dea
Source dataset
uspto-grants-1982_01
Patent number
US04309566

Reaction notes

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