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Cyclohexane → 4-Hydroxy-3-(6-methylpyrid-2-yl)-4-propylthiazolidine-2-thione

HRID 261197
ノート
印刷プレビュー

反応式

HRID 261197 の反応式
Cl[CH2:2][C:3](=[O:7])[CH2:4][CH2:5][CH3:6].[CH3:8][C:9]1[N:14]=[C:13]([NH:15][C:16](=[S:18])[S-:17])[CH:12]=[CH:11][CH:10]=1.C([NH+](CC)CC)C.C1CCCCC1>C(#N)C>[OH:7][C:3]1([CH2:4][CH2:5][CH3:6])[CH2:2][S:18][C:16](=[S:17])[N:15]1[C:13]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:8])[N:14]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8078CyclohexaneHCID 112864631-Chloropentan-2-oneHCID 20393055Triethylammonium 6-methylpyrid-2-yldithiocarbamate

生成物 1

HCID 203930574-Hydroxy-3-(6-methylpyrid-2-yl)-4-propylthiazolidine-2-thione収率 80.6%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
10 °C

実験手順

1-Chloropentan-2-one (12.1 g) is added to a suspension of triethylammonium (6-methylpyrid-2-yl)dithiocarbamate (28.5 g) in anhydrous acetonitrile (200 cc) at a temperature between 15° and 25° C. The reaction is continued for 2 hours at 20°-25° C. The insoluble triethylamine hydrochloride is removed by filtration and washed twice with diethyl ether (60 cc. total). The solvents are evaporated under reduced pressure (20 mm.Hg) at 40° C. The residual oil is dissolved in a mixture of diethyl ether (100 cc) and methylene chloride (50 cc); the organic solution is washed twice with distilled water (total 100 cc), dried over sodium sulphate and evaporated. The crystals obtained (25.4 g; m.p. about 70° C.) are dissolved in boiling cyclohexane (500 cc) and the boiling solution is filtered. After cooling for 1 hour at about 10° C., the resulting crystals are separated by filtration, washed twice with cyclohexane (total 120 cc) cooled to 10° C., and dried under reduced pressure (0.1 mm.Hg) at 40° C. 4-Hydroxy-3-(6-methylpyrid-2-yl)-4-propylthiazolidine-2-thione (21.6 g), melting at 83° C., is thus obtained.

後処理

  1. customThe insoluble triethylamine hydrochloride is removed by filtration
  2. washwashed twice with diethyl ether (60 cc. total)
  3. customThe solvents are evaporated under reduced pressure (20 mm.Hg) at 40° C
  4. dissolutionThe residual oil is dissolved in a mixture of diethyl ether (100 cc) and methylene chloride (50 cc)
  5. washthe organic solution is washed twice with distilled water (total 100 cc)
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. customThe crystals obtained (25.4 g; m.p. about 70° C.)
  9. dissolutionare dissolved
  10. filtrationthe boiling solution is filtered
  11. customthe resulting crystals are separated by filtration
  12. washwashed twice with cyclohexane (total 120 cc)
  13. temperaturecooled to 10° C.
  14. customdried under reduced pressure (0.1 mm.Hg) at 40° C

出典と根拠

ORDレコード
ord-0b779f0c9f4240cd84a0040ec3124e21
出典データセット
uspto-grants-1979_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04164579

反応ノート

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