Ammonia → 5-Methyl-2-(3-pyridyl)-oxazole

HRID 1600447Notes

Reaction equation

HRID 1600447 reaction equation
[C:1]([CH2:4][NH:5][C:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[N:9][CH:8]=1)(=O)[CH3:2].N>S(=O)(=O)(O)O>[CH3:2][C:1]1[O:13][C:6]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[N:5][CH:4]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 19612493N-Acetylmethyl-nicotinamide

Product 1

HCID 196125075-Methyl-2-(3-pyridyl)-oxazole

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
120 °C

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%).

Workup

  1. temperatureAfter cooling the mixture
  2. additionwas poured over ice
  3. extractionExtraction with 3×400 ml of dichloromethane
  4. dry with materialdrying of the combined organic phase over magnesium sulphate, and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-7657e5b7bf7749b5ade477c43dc5633b
Source dataset
uspto-grants-1999_11
Patent number
USRE036374

Reaction notes

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