Acetamide → HCID 13115425, compound

HRID 1075319Notes

Reaction equation

HRID 1075319 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:11]=O.[C:13]([NH2:16])(=[O:15])[CH3:14]>S(=O)(=O)(O)O>[CH3:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=1[CH2:11][NH:16][C:13](=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 178AcetamideHCID 712FormaldehydeHCID 74734-Nitrotoluene

Product 1

HCID 13115425HCID 13115425, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of p-nitrotoluene (0.85 g; 0.05 mol) and para-formaldehyde (1.6 g; 0.05 mol) in concentrated sulfuric acid is added acetamide (8.85 g; 0.15 mol) in increments. This solution is stirred at room temperature for 18 hours. The reaction mixture is then poured onto ice. A precipitate is obtainined which is removed by filtration. This solid material is then mixed with butyl acetate, heated, and filtered while hot to remove insolubles. After cooling, 7.8 g (i.e., 75% yield) of product crystallizes out of solution. The product has the following characteristics: melting point of 141° to 143° C.; i.r. 3275, 1640 and 1660 cm-1 (sh); mass. spec. m/e 208.

Workup

  1. additionThe reaction mixture is then poured onto ice
  2. customis removed by filtration
  3. additionThis solid material is then mixed with butyl acetate
  4. temperatureheated
  5. filtrationfiltered while hot
  6. customto remove insolubles
  7. temperatureAfter cooling
  8. custom7.8 g (i.e., 75% yield) of product crystallizes out of solution

Sources & evidence

ORD record
ord-d5d1e6fc8ccf48e894ba9d715754b089
Source dataset
uspto-grants-1983_07
Patent number
US04395577

Reaction notes

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