Hydrochloric Acid → alpha-chloro-alpha-(2,4-dichlorophenyl)-acetic acid-N-2-butyl-N-methyl amide

HRID 848750Notes

Reaction equation

HRID 848750 reaction equation
[CH3:1][CH:2]([NH:5][CH3:6])[CH2:3][CH3:4].[Cl:7][CH:8]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[Cl:19])[C:9](Cl)=[O:10].Cl>O1CCOCC1>[CH3:1][CH:2]([N:5]([CH3:6])[C:9](=[O:10])[CH:8]([Cl:7])[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[Cl:19])[CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 111026N-Methyl-2-butanamineHCID 20564372alpha-Chloro-alpha-(2,4-dichlorophenyl)-acetyl chloride

Product 1

HCID 20564362alpha-chloro-alpha-(2,4-dichlorophenyl)-acetic acid-N-2-butyl-N-methyl amideYield 64.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

While stirring, 15.2 g of N-2-butyl-N-methylamine is dripped into a solution of 22.4 g of α-chloro-α-(2,4-dichlorophenyl)-acetyl chloride (see a)) in 100 ml of dioxane. After the exothermic reaction has subsided, the mixture is stirred overnight and then poured into 700 ml of ice water; the resultant mixture is acidified with dilute hydrochloric acid and the oil which has precipitated is extracted 8 times, each time with 100 ml of dichloromethane. The extracts are combined, dried over magnesium sulfate and concentrated; there is obtained 17.2 g of α-chloro-α-(2,4-dichlorophenyl)-acetic acid-N-2-butyl-N-methyl amide as a colorless oil.

Workup

  1. customAfter the exothermic reaction
  2. stirringthe mixture is stirred overnight
  3. customthe oil which has precipitated
  4. extractionis extracted 8 times
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4cd6978016b644e3867acf9699e09439
Source dataset
uspto-grants-1981_10
Patent number
US04297364

Reaction notes

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