2-Aminothiazole → 2-(1H-pyrrol-1-yl)-1,3-thiazole
Reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[CH3:7][CH:8]1[CH2:12][CH2:11]C(C)O1.[OH-].[Na+]>C(O)(=O)C>[S:3]1[CH:4]=[CH:5][N:6]=[C:2]1[N:1]1[CH:11]=[CH:12][CH:8]=[CH:7]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 55.5 g (0.5 mole) 2-aminothiazole (90% pure) and 66 g (0.5 mole) 2,5-dimethyltetrahydrofuran is placed in a 1-liter 3-neck flask equipped with a stirrer, addition funnel, thermometer, and condenser, and 200 ml glacial acetic acid is added dropwise with stirring while maintaining the temperature below 20°C. After stirring for an additional 15 minutes, the reaction mixture is refluxed for 30 minutes and then cooled, made basic (pH 9-10) with 375 ml 30% sodium hydroxide, and steam-distilled to yield 1500 ml distillate.
Workup
- customis placed in a 1-liter 3-neck flask
- customequipped with a stirrer, addition funnel
- temperaturewhile maintaining the temperature below 20°C
- stirringAfter stirring for an additional 15 minutes
- temperaturethe reaction mixture is refluxed for 30 minutes
- temperaturecooled
- distillationsteam-distilled
- customto yield 1500 ml distillate
Sources & evidence
- ORD record
- ord-a913f47527dd42d68ca9df402916385f
- Source dataset
- uspto-grants-1976_09
- Patent number
- US03980089
Reaction notes
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