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

HRID 249299노트

반응식

HRID 249299 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-600cc9ec9ab44b9e815d072a54b25c5b
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05214051

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