Formaldehyde → HCID 13175475, compound

HRID 1075323Notes

Reaction equation

HRID 1075323 reaction equation
[C:1]([NH2:5])(=[O:4])[CH:2]=[CH2:3].[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)([O-:8])=[O:7].[CH2:16]=O>S(=O)(=O)(O)O>[CH3:15][C:12]1[CH:13]=[CH:14][C:9]([N+:6]([O-:8])=[O:7])=[CH:10][C:11]=1[CH2:16][NH:5][C:1](=[O:4])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6579AcrylamideHCID 74734-Nitrotoluene

Product 1

HCID 13175475HCID 13175475, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Acrylamide (7.10 g; 0.10 mol) is added in small increments to a stirred solution of p-nitrotoluene (1.85 g; 0.05 mol) and paraformaldehyde (1.6 g; 0.05 mol) in concentrated sulfuric acid (60 ml). This reaction mixture is stirred for 24 hours at room temperature and then poured onto ice. A precipitate results which is collected and recrystallized from ethyl acetate to give 4.4 g of product as colorless crystals. This product has the following characteristics: melting point of 155° to 158.5° C.; i.r. 3230, 1620, 1655, 1660 cm-1 (sh).

Workup

  1. additionpoured onto ice
  2. customA precipitate results which
  3. customis collected
  4. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9f1c24eaa16843b196c8bdaeba83de99
Source dataset
uspto-grants-1983_07
Patent number
US04395577

Reaction notes

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