Benzene → 2-[1-(4-chlorophenyl)ethylideneamino]oxyacetic Acid

HRID 2058452Notes

Reaction equation

HRID 2058452 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6](=[N:8][O:9][CH2:10][C:11](Cl)=[O:12])[CH3:7])=[CH:4][CH:3]=1.Cl.[NH2:17][CH2:18][CH2:19][OH:20].[C:21](=[O:24])(O)[O-:22].[K+].[CH:26]1C=CC=CC=1>CN(C)C=O.C(OCC)C>[C:21]([NH:17][CH2:18][CH2:19][O:20][C:11](=[O:12])[CH2:10][O:9][N:8]=[C:6]([CH3:7])[C:5]1[CH:14]=[CH:15][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:24])[CH3:26].[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6](=[N:8][O:9][CH2:10][C:11]([OH:22])=[O:12])[CH3:7])=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 700EthanolamineHCID 516893Potassium BicarbonateHCID 53689620HCID 53689620, compound

Product 2

HCID 28212572-[1-(4-chlorophenyl)ethylideneamino]oxyacetic AcidHCID 54001377HCID 54001377, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1.2 g of (4-chloro-α-methylbenzylidene) amino-oxyacetyl chloride in 3 ml of benzene was added whilst stirring to a solution of 0.45 g of the hydrochloride of 2-aminoethanol in 10 ml of dimethylformamide. After the reaction mixture had been allowed to stand at room temperature for 24 hours it was mixed with 25 ml of diethylether and 25 ml of a 10% solution of potassium bicarbonate. On termination of the carbondioxide evolution the mixture was separated and the ethereal layer was washed another time with 10 ml of water. The ethereal solution was extracted with 6 ml of 2 N-hydrochloric acid and then twice with altogether 15 ml of water. The latter three extracts were combined and mixed with 2 g of potassium bicarbonate. On termination of the evolution of carbon dioxide the mixture was twice extracted with diethylether. The ethereal extracts were dried with anhydrous sodiumsulphate, concentrated by evaporation and then neutralized with 2 N alcoholic hydrochloric acid. The addition of ether to the neutralized solution resulted in the crystallisation of the hydrochloride of the (2-aminoethyl)ester of (4-chloro-α-methylbenzylidene) aminooxyacetic acid. Melting point 167°-169° C. with decomposition.

Workup

  1. customOn termination of the carbondioxide evolution the mixture was separated
  2. washthe ethereal layer was washed another time with 10 ml of water
  3. extractionThe ethereal solution was extracted with 6 ml of 2 N-hydrochloric acid
  4. additionmixed with 2 g of potassium bicarbonate
  5. extractionOn termination of the evolution of carbon dioxide the mixture was twice extracted with diethylether
  6. dry with materialThe ethereal extracts were dried with anhydrous sodiumsulphate
  7. concentrationconcentrated by evaporation
  8. additionThe addition of ether to the neutralized solution

Sources & evidence

ORD record
ord-7fc2108bd48342f5a69a10825cd061a2
Source dataset
uspto-grants-1982_03
Patent number
US04317835

Reaction notes

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