2-Aminothiazole → 2-pyrrol-1-yl-1,3-thiazole

HRID 1576278Notes

Reaction equation

HRID 1576278 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]1

Participants

5

Reactant 3

HCID 21552-AminothiazoleHCID 138552,5-DimethyltetrahydrofuranHCID 14798Sodium Hydroxide

Product 1

HCID 2986802-pyrrol-1-yl-1,3-thiazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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

  1. customis placed in a 1-liter 3-neck flask
  2. customequipped with a stirrer, addition funnel
  3. temperaturewhile maintaining the temperature below 20°C
  4. stirringAfter stirring for an additional 15 minutes
  5. temperaturethe reaction mixture is refluxed for 30 minutes
  6. temperaturecooled
  7. distillationsteam-distilled
  8. 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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