Acetamide → N-(2-ethyl-5-nitrobenzyl)acetamide

HRID 1075322Notes

Reaction equation

HRID 1075322 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1)[CH3:2].[C:12]([NH2:15])(=[O:14])[CH3:13].[CH2:16]=O>S(=O)(=O)(O)O>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([N+:9]([O-:11])=[O:10])=[CH:7][C:8]=1[CH2:16][NH:15][C:12](=[O:14])[CH3:13])[CH3:2]

Participants

5

Reactant 3

HCID 178AcetamideHCID 712FormaldehydeHCID 7480Benzene, 1-ethyl-4-nitro-

Product 1

HCID 13175474N-(2-ethyl-5-nitrobenzyl)acetamideYield 56%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
55 °C

Procedure

4-Ethylnitrobenzene (7.55 g; 0.05 mol) is added in small increments to a stirred solution of acetamide (5.9 g; 0.05 mol) and paraformaldehyde (1.6 g; 0.05 mol) in concentrated sulfuric acid (60 ml). This reaction mixture is stirred for 17 hours at 55° C. and then poured onto ice. A precipitate results which is recrystallized from butyl acetate to give 6.2 g (i.e., 56% yield) of product. This product has the following characteristics: melting point of 123° to 128° C.; i.r. 3275, 1640 and 1660 cm-1 (sh); mass. spec. m/e 222.

Workup

  1. additionpoured onto ice
  2. customA precipitate results which
  3. customis recrystallized from butyl acetate
  4. customto give 6.2 g (i.e., 56% yield) of product

Sources & evidence

ORD record
ord-c85deddd7de14a0cb4aed6548957c3dc
Source dataset
uspto-grants-1983_07
Patent number
US04395577

Reaction notes

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