p-Toluenesulfonic acid → HCID 15049980, compound

HRID 649545Notes

Reaction equation

HRID 649545 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[CH2:7]([O:9][CH:10](OCC)[O:11][CH2:12][CH3:13])[CH3:8].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH2:7]([O:9][CH:10]([O:11][CH2:12][CH3:13])[N:5]1[CH:6]=[C:2]([CH3:1])[N:3]=[CH:4]1)[CH3:8]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31214Ethyl orthoformateHCID 178418800HCID 178418800, compound

Product 1

HCID 15049980HCID 15049980, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Methylimidazole (16.4 g), triethylorthoformate (118.4 g), and p-toluene sulphonic acid (1 g) were mixed and heated at 130° until evolution of ethanol ceased (approximately 2 hours). Volatile material was removed in vacuo and the residue was distilled under vacuum from anhydrous sodium carbonate (1 g) to afford the title compound, b.p. 126°-130°/5 mm (22.06 g). The product was characterised spectroscopically and used without further purification (Preparation 26).

Workup

  1. custom(approximately 2 hours)
  2. customVolatile material was removed in vacuo
  3. distillationthe residue was distilled under vacuum from anhydrous sodium carbonate (1 g)

Sources & evidence

ORD record
ord-fd033988f8974c71a6eb0b2e990cc1b4
Source dataset
uspto-grants-1988_04
Patent number
US04740513

Reaction notes

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