Isopropanol → (RS)-6-Hydroxymethyl-5-[(pyrid-3-yl)thiocarbamoyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

HRID 443834ノート

反応式

HRID 443834 の反応式
[N:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)=[C:2]=[S:3].[OH:10][CH2:11][CH:12]1[NH:17][CH2:16][C:15]2[CH:18]=[CH:19][S:20][C:14]=2[CH2:13]1.C(O)(C)C.C(OC(C)C)(C)C>C(O)C>[OH:10][CH2:11][CH:12]1[N:17]([C:2](=[S:3])[NH:1][C:4]2[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=2)[CH2:16][C:15]2[CH:18]=[CH:19][S:20][C:14]=2[CH2:13]1

参加物

6

反応物 4

HCID 3776IsopropanolHCID 7914Diisopropyl EtherHCID 27372423-Pyridyl isothiocyanateHCID 12939919(RS)-6-hydroxymethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

生成物 1

HCID 12939920(RS)-6-Hydroxymethyl-5-[(pyrid-3-yl)thiocarbamoyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridine収率 75.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
20 °C

実験手順

A solution of 3-isothiocyanatopyridine (1.36 g) in absolute ethanol (40 cc) is added dropwise, at a temperature of about 0° C., to a solution of (RS)-6-hydroxymethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (1.69 g) in absolute ethanol (60 cc). The resulting solution is stirred for 20 hours at a temperature of about 20° C. and the solid formed is then filtered off. The filtrate is evaporated to dryness under reduced pressure (25 mm Hg; 3.3 kPa) at 40° C. and a white solid is obtained which is combined with the solid isolated by filtration. These solids are dissolved in a mixture, heated under reflux, of isopropanol and diisopropyl ether (1:2 by volume; 130 cc) and the solution, after cooling, is kept at +5° C. for 20 hours. The resulting crystals are filtered off, washed with diisopropyl ether (50 cc) and dried at 20° C. under reduced pressure (0.1 mm Hg; 0.013 kPa). (RS)- 6-Hydroxymethyl-5-[(pyrid-3-yl)thiocarbamoyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (2.3 g) is thus obtained in the form of white crystals melting at 186° C.

後処理

  1. customthe solid formed
  2. filtrationis then filtered off
  3. customThe filtrate is evaporated to dryness under reduced pressure (25 mm Hg; 3.3 kPa) at 40° C.
  4. customa white solid is obtained which
  5. customisolated by filtration
  6. dissolutionThese solids are dissolved in a mixture
  7. temperatureheated
  8. temperaturethe solution, after cooling
  9. waitis kept at +5° C. for 20 hours
  10. filtrationThe resulting crystals are filtered off
  11. washwashed with diisopropyl ether (50 cc)
  12. customdried at 20° C. under reduced pressure (0.1 mm Hg; 0.013 kPa)

出典と根拠

ORDレコード
ord-9e6a3750a6cd46748b9b9fe248579ceb
出典データセット
uspto-grants-1981_04
特許番号
US04261999

反応ノート

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