2-Chloro-N,N-dimethylethylamine → HCID 85439121, compound

HRID 2058451Notes

Reaction equation

HRID 2058451 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([CH3:6])[CH3:5].[Na].[Cl:8][C:9]1[CH:22]=[CH:21][C:12]([C:13](=[N:15][O:16][CH2:17][C:18]([OH:20])=[O:19])[CH3:14])=[CH:11][CH:10]=1>CN(C)C=O.O>[ClH:1].[CH3:5][N:4]([CH3:6])[CH2:3][CH2:2][O:20][C:18](=[O:19])[CH2:17][O:16][N:15]=[C:13]([CH3:14])[C:12]1[CH:21]=[CH:22][C:9]([Cl:8])=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 28212572-[1-(4-chlorophenyl)ethylideneamino]oxyacetic AcidHCID 5360545Sodium

Product 1

HCID 85439121HCID 85439121, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4.3 g of 2-chloro-N,N-dimethyl ethylamine was added to a suspension of 10 g of the sodium salt of (4-chloro-α-methylbenzylidene)amino-oxyacetic acid in 30 ml of dimethylformamide. The mixture was stirred for 72 hours. It was then diluted with water and extracted with diethylether. The resulting ethereal solution was extracted with 20 ml of 2 N hydrochloric acid. The acid extract was then made basic with 30 ml of 2 N sodium hydroxide and extracted with diethylether. The latter ethereal extract was washed, dried over anhydrous sodium sulphate and after concentration by evaporation neutralized with alcoholic hydrochloric acid. When diethylether was added the hydrochloride of the (2-dimethyl-aminoethyl)ester of (4-chloro-α-methylbenzylidene) aminooxyacetic acid crystallized out. It was recrystallized from an alcohol-ether mixture; melting point 160°-162° C. with decomposition.

Workup

  1. extractionextracted with diethylether
  2. extractionThe resulting ethereal solution was extracted with 20 ml of 2 N hydrochloric acid
  3. extractionThe acid extract
  4. extractionextracted with diethylether
  5. extractionThe latter ethereal extract
  6. washwas washed
  7. dry with materialdried over anhydrous sodium sulphate
  8. concentrationafter concentration
  9. customby evaporation
  10. additionWhen diethylether was added the hydrochloride of the (2-dimethyl-aminoethyl)ester of (4-chloro-α-methylbenzylidene) aminooxyacetic acid
  11. customcrystallized out
  12. customIt was recrystallized from an alcohol-ether mixture

Sources & evidence

ORD record
ord-d54dc5e7ed944e378a49b32be1e283c1
Source dataset
uspto-grants-1982_03
Patent number
US04317835

Reaction notes

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