N,N-Dimethylaniline → HCID 21286895, compound

HRID 745702Notes

Reaction equation

HRID 745702 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].CN(C)C1C=CC=CC=1.[Br:19][CH2:20][C:21](Br)=[O:22]>CC(C)=O>[OH:9][C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[NH:1][C:21](=[O:22])[CH2:20][Br:19]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 72652-Amino-4-chlorophenolHCID 61147Bromoacetyl bromide

Product 1

HCID 21286895HCID 21286895, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 2-amino-4-chlorophenol (19.50 g.) and N,N-dimethylaniline (19.90 g.) in dry acetone (200 ml.) was added dropwise bromoacetyl bromide (33.2 g.) over a period of 15 minutes under ice-cooling at below 10° C. with stirring and stirring was continued for 45 minutes at the same temperature. The reaction mixture was evaporated and to the residue were added ethyl acetate and water. The ethyl acetate layer was washed with 5% hydrochloric acid (twice), water, 5% aqueous solution of sodium bicarbonate, water (twice) and a saturated aqueous solution of sodium chloride successively, dried over magnesium sulfate, treated with activated charcoal and then evaporated. The residue was recrystallized from a mixture of ethyl acetate and diisopropyl ether to give the title compound (18.91 g.).

Workup

  1. temperaturecooling at below 10° C.
  2. stirringstirring
  3. customThe reaction mixture was evaporated and to the residue
  4. additionwere added ethyl acetate and water
  5. washThe ethyl acetate layer was washed with 5% hydrochloric acid (twice), water, 5% aqueous solution of sodium bicarbonate, water (twice) and a saturated aqueous solution of sodium chloride successively
  6. dry with materialdried over magnesium sulfate
  7. additiontreated with activated charcoal
  8. customevaporated
  9. customThe residue was recrystallized from a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-ccfda3c050574752a971ccaadb97e045
Source dataset
uspto-grants-1986_07
Patent number
US04599426

Reaction notes

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