Water → 4'-Dimethylaminoacetanilide

HRID 2093040

Reaction equation

HRID 2093040 reaction equation
[CH3:1][N:2]([CH3:10])[C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:18](OC(=O)C)(=[O:20])[CH3:19].O>ClCCl>[CH3:1][N:2]([CH3:10])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:18](=[O:20])[CH3:19])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7472N,N-dimethyl-p-phenylenediamineHCID 7918Acetic AnhydrideHCID 8471Triethylamine

Product 1

HCID 819684'-DimethylaminoacetanilideYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N,N-dimethylbenzene-1,4-diamine (1.0 eq) in dichloromethane, triethylamine (2.2 eq) was added at 0° C. and stirred for 15 min. To the above mixture was then added a solution of acetic anhydride (1.0 eq) in dichloromethane at 0° C., after addition the reaction was continued at room temperature for 5 hrs. Water was added and the organic layer was separated, dried over anhydrous Na2SO4, concentrated under reduced pressure to afford crude product, which, on purification by column chromatography afforded the desired N-[4-(dimethylamino)phenyl]acetamide. (Yield=69%)

Workup

  1. additionafter addition the reaction
  2. waitwas continued at room temperature for 5 hrs
  3. customthe organic layer was separated
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto afford crude product, which
  7. customon purification by column chromatography

Sources & evidence

ORD record
ord-caed95fe1a9247fd8670bf899b7624dc
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Linked notes

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