Formaldehyde → HCID 18770563, compound

HRID 479526Notes

Reaction equation

HRID 479526 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.C=O.[NH:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[N:14]1.[O-]S([O-])(=O)=O.[Mg+2].[C:28]1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N:13]1([CH2:28][NH:8][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[N:14]1

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 6101p-Toluenesulfonic acidHCID 120844-ChlorobenzamideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 178418385HCID 178418385, compound

Product 1

HCID 18770563HCID 18770563, compoundYield 836.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 4-chlorobenzamide (2.61 g, 16.8 mmol), paraformaldehyde (0.50 g, 16.8 mmol), benzotriazole (2.00 g, 16.8mmol), and MgSO4 (2.00 g, 16.6 mmol) in toluene (50 mL) was treated with p-toluenesulfonic acid (168 mg, 0.88 mmol). The mixture was heated at reflux for 4 hours, cooled to ambient temperature, filtered and concentrated to dryness. The crude material was purified by trituration with diethyl ether to provide 2.11 g of the desired product as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 4 hours
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe crude material was purified by trituration with diethyl ether

Sources & evidence

ORD record
ord-0f0970e0673244ab9e2f92d021cdb043
Source dataset
uspto-grants-2003_11
Patent number
US06645968B2

Reaction notes

Loading…