Acetyl chloride → Acetamide, N-(2,4,6-trimethylphenyl)- (9CI)

HRID 1610919Notes

Reaction equation

HRID 1610919 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[NH2:10].[C:11](Cl)(=[O:13])[CH3:12].CCN(CC)CC>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[NH:10][C:11](=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 69132,4,6-TrimethylanilineHCID 8471Triethylamine

Product 1

HCID 21170Acetamide, N-(2,4,6-trimethylphenyl)- (9CI)Yield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2,4,6-trimethyl-phenylamine (1) (50 g, 0.370 moles) in CH2Cl2 (500 mL) was cooled to 0° C. (ice-water bath). To this was added acetyl chloride (29.8 g, 27 mL, 380 mmol) during 5 minutes via an addition funnel; this was followed by portion-wise addition of Et3N (38.5 g, 53 mL, 380 mmol). The ice-bath was removed and the solution was allowed to warm to room temperature and stir for 2 h. The resultant ivory colored solid was collected by filtration and dried in vacuo. To remove residual Et3N.HCl, the solid was suspended H2O (600 mL) stirred for 0.5 h, collected by filtration and dried to a constant weight. The original organic filtrate was washed with H2O (3×100 mL) and brine (1×100 mL), dried (MgSO4), filtered and concentrated providing additional product. Combined with material collected from the water afforded 60.2 g (99% yield) of the desired acetamide. RP-HPLC Method: 2-100 B in 2 minutes.

Workup

  1. customThe ice-bath was removed
  2. filtrationThe resultant ivory colored solid was collected by filtration
  3. customdried in vacuo
  4. customTo remove residual Et3N.HCl
  5. stirringstirred for 0.5 h
  6. filtrationcollected by filtration
  7. customdried to a constant weight
  8. washThe original organic filtrate was washed with H2O (3×100 mL) and brine (1×100 mL)
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customproviding additional product
  13. customcollected from the water

Sources & evidence

ORD record
ord-89b551b460df4290837e3851d7e50851
Source dataset
uspto-grants-2006_01
Patent number
US06984652B2

Reaction notes

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