Thiourea → 1-(2-Amino-6,7-dihydro-4H-thiazolo[5,4-c]pyridin-5-yl)-ethanone

HRID 249299Notes

Reaction equation

HRID 249299 reaction equation
Br.[C:2]([N:5]1[CH2:10][CH2:9][C:8](=O)[CH:7](Br)[CH2:6]1)(=[O:4])[CH3:3].[NH2:13][C:14]([NH2:16])=[S:15]>C(O)C>[C:2]([N:5]1[CH2:10][CH2:9][C:8]2[N:13]=[C:14]([NH2:16])[S:15][C:7]=2[CH2:6]1)(=[O:4])[CH3:3]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 197611761-Acetyl-3-bromopiperidin-4-one hydrobromide

Product 1

HCID 150176501-(2-Amino-6,7-dihydro-4H-thiazolo[5,4-c]pyridin-5-yl)-ethanoneYield 10.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-Acetyl-3-bromo-4-piperidone hydrobromide (3.0 g, 9.9 mmol) was added slowly to a solution of thiourea (756 mg, 9.9 mmol) in dry ethanol (13.5 ml) at 60°. After completion of the addition, the reaction mixture was allowed to stir at 40° for 1 hour; the ethanol was then distilled off at atmospheric pressure, and the residue was heated to 160°-170° for 20 minutes. The reaction mixture was then cooled and dissolved in water, neutralized with saturated aqueous sodium bicarbonate, and extracted three times with chloroform. The combined organic layers were dried over sodium sulfate, filtered and concentrated to give an oil. Purification was effected by flash column chromatography (9:1 chloroform:methanol) to provide the title product as a solid (200 mg, 1.0 mmol, 10% yield).

Workup

  1. additionAfter completion of the addition
  2. distillationthe ethanol was then distilled off at atmospheric pressure
  3. temperaturethe residue was heated to 160°-170° for 20 minutes
  4. temperatureThe reaction mixture was then cooled
  5. dissolutiondissolved in water
  6. extractionextracted three times with chloroform
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give an oil
  11. customPurification

Sources & evidence

ORD record
ord-600cc9ec9ab44b9e815d072a54b25c5b
Source dataset
uspto-grants-1993_05
Patent number
US05214051

Reaction notes

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