Formaldehyde → HCID 13115425, compound

HRID 1075320Notes

Reaction equation

HRID 1075320 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:11][C:12]([NH:14][C:15](C)=O)=[O:13].C=O>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[CH2:15][NH:14][C:12](=[O:13])[CH3:11]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 74734-NitrotolueneHCID 12263Diacetamide

Product 1

HCID 13115425HCID 13115425, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of p-nitrotoluene (2.74 g; 0.02 mol) and diacetamide (4.24 g; 0.04 mol) in concentrated sulfuric acid (20 ml) is added aqueous formaldehyde (37%; 1.6 g; 0.02 mol) dropwise with stirring. The reaction mixture is stirred at room temperature for 17 hours, heated to 55° C. for 8 hours and then to 85° C. for 19 hours. The mixture is then poured onto ice. The resulting colorless precipitate is removed by filtration and recrystallized from aqueous ethanol to give 2.7 g of product (65% yield) having a melting point of 133° to 137.5° C.

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 17 hours
  2. additionThe mixture is then poured onto ice
  3. customThe resulting colorless precipitate is removed by filtration
  4. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-e87131df6bfa48e1bf1bef72c29fee39
Source dataset
uspto-grants-1983_07
Patent number
US04395577

Reaction notes

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