Reaction #1687629

ord-7657e5b7bf7749b5ade477c43dc5633b

Reaction equation

CC(=O)CNC(=O)c1cccnc1
73
CC(=O)CNC(=O)c1cccnc1
N-Acetylmethyl-nicotinamide
N
ammonia
→
Cc1cnc(-c2cccnc2)o1
74
Cc1cnc(-c2cccnc2)o1
5-Methyl-2-(3-pyridyl)-oxazole

Reactants

CC(=O)CNC(=O)c1cccnc1
73
CC(=O)CNC(=O)c1cccnc1
N-Acetylmethyl-nicotinamide
N
ammonia

Reagents

None

Solvents

O=S(=O)(O)O
sulphuric acid

Conditions

Temperature
120°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureAfter cooling the mixture
  2. 2
    workup.ADDITIONwas poured over ice
  3. 3
    ExtractionExtraction with 3×400 ml of dichloromethane
  4. 4
    Dryingdrying of the combined organic phase over magnesium sulphate, and removal of the solvent in vacuo

Procedure

A mixture of 20 g (0.110 mol) of 73 and 100 ml of conc. sulphuric acid was heated to 120° C. for 4 h. After cooling the mixture was poured over ice followed by basification with ammonia. Extraction with 3×400 ml of dichloromethane, drying of the combined organic phase over magnesium sulphate, and removal of the solvent in vacuo gave crude 74 as a red oil, which was sufficiently pure. Yield: 17 g (0.100 mol, 97%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: USRE036374uspto-grants-1999_11