Water → N-(4-amino-2,5-dimethylphenyl)acetamide

HRID 2181589Notes

Reaction equation

HRID 2181589 reaction equation
[C:1]1([CH3:10])[C:2](N)=[C:3]([NH2:8])[C:4]([CH3:7])=[CH:5][CH:6]=1.[CH:11]([NH:14]C(C)C)(C)[CH3:12].C(Cl)(=[O:20])C.O>ClCCl>[NH2:8][C:3]1[C:4]([CH3:7])=[CH:5][C:6]([NH:14][C:11](=[O:20])[CH3:12])=[C:1]([CH3:10])[CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 7912DiisopropylamineHCID 37769873,6-Dimethylbenzene-1,2-diamine

Product 1

HCID 22481227N-(4-amino-2,5-dimethylphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of p-xylenediamine (2.0 g) in dichloromethane (200 ml) maintained below 10° C. was added N,N-diisopropylamine (2.52 ml) followed by the dropwise addition of acetylchloride (1.15 g). The mixture was allowed to attain room temperature and stirred overnight. Water (120 ml) was added and the suspension filtered. The filtered solid was washed with dichloromethane (2×100 ml) and water (100 ml). All filtrates were combined and the organic layer separated. The organic layer was washed with water, dried (MgSO4) and evaporated to give the title product as a solid, m.p. 133-5° C.

Workup

  1. customto attain room temperature
  2. filtrationthe suspension filtered
  3. washThe filtered solid was washed with dichloromethane (2×100 ml) and water (100 ml)
  4. customthe organic layer separated
  5. washThe organic layer was washed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-fd3c8dfdcdfc49c5952ff0ed28415aa8
Source dataset
uspto-grants-2005_05
Patent number
US06893650B1

Reaction notes

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