Hydrochloric Acid → HCID 20564369, compound

HRID 848751Notes

Reaction equation

HRID 848751 reaction equation
[CH:1]([NH:4][CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[Cl:8][CH:9]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[C:10](Cl)=[O:11].Cl>O1CCOCC1>[CH:1]([N:4]([CH:5]([CH3:7])[CH3:6])[C:10](=[O:11])[CH:9]([Cl:8])[C:13]1[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 2056437875188-06-6

Product 1

HCID 20564369HCID 20564369, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

While stirring, 22.3 g of diisopropylamine is dripped into a solution of 24.5 g of α-chloro-α-(4-chlorophenyl)-acetyl chloride (see a)) in 50 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 separates out is extracted 8 times, each time with 100 ml of dichloromethane. The combined extracts are washed twice with sodium carbonate solution, dried over magnesium sulfate and concentrated. There is obtained 27.2 g of α-chloro-α-(4-chlorophenyl)-acetic acid diisopropyl amide as a brownish oil.

Workup

  1. customAfter the exothermic reaction
  2. stirringthe mixture is stirred overnight
  3. extractionthe oil which separates out is extracted 8 times
  4. washThe combined extracts are washed twice with sodium carbonate solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6d934844258c4921ad3089352044e6b4
Source dataset
uspto-grants-1981_10
Patent number
US04297364

Reaction notes

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