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

HRID 2247931ノート

反応式

HRID 2247931 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e89b21e3c9ed4e5994a999317c13a6d8
出典データセット
uspto-grants-1991_08
特許番号
US05037834

反応ノート

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