Water → N-[4-(Propan-2-yl)phenyl]ethanimidic acid

HRID 2093037Notes

Reaction equation

HRID 2093037 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.[C:18](OC(=O)C)(=[O:20])[CH3:19].O>ClCCl>[CH:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:18](=[O:20])[CH3:19])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 74644-IsopropylanilineHCID 7918Acetic AnhydrideHCID 8471Triethylamine

Product 1

HCID 258025N-[4-(Propan-2-yl)phenyl]ethanimidic acidYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-isopropylaniline (1.0 eq) in dichloromethane at 0° C., triethylamine (2.2 eq) was added and stirred for 15 min. Then, acetic anhydride (1.0 eq) in dichloromethane was added 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-isopropylphenyl)acetamide. (Yield=95%)

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-94693ed26b72423c9b046dfbbbc15112
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

Loading…