Ethanol → 4-Hydroxy-4-methyl-3-(6-methylpyrid-2-yl)-thiazolidine-2-thione

HRID 261195ノート

反応式

HRID 261195 の反応式
Cl[CH2:2][C:3](=[O:5])[CH3:4].[CH3:6][C:7]1[N:12]=[C:11]([NH:13][C:14](=[S:16])[S-:15])[CH:10]=[CH:9][CH:8]=1.C([NH+](CC)CC)C.C(O)C>CN(C)C=O>[OH:5][C:3]1([CH3:4])[CH2:2][S:16][C:14](=[S:15])[N:13]1[C:11]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:6])[N:12]=1

参加物

5

反応物 3

HCID 702EthanolHCID 6571ChloroacetoneHCID 20393055Triethylammonium 6-methylpyrid-2-yldithiocarbamate

生成物 1

HCID 203930694-Hydroxy-4-methyl-3-(6-methylpyrid-2-yl)-thiazolidine-2-thione

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
2 °C

実験手順

Chloroacetone (13.9 cc) is added to a solution of triethylammonium (6-methylpyrid-2-yl)dithiocarbamate (50.0 g) in dimethylformamide (250 cc) at a temperature between 15 and 23° C. The reaction is continued for 3 hours at 20°-23° C. After filtration and evaporation of the dimethylformamide under reduced pressure (0.1 mm.Hg) at 45° C., the residual oil is dissolved in ethyl acetate (500 cc); the organic solution is washed with distilled water (100 cc), dried over sodium sulphate, treated with decolorising charcoal (2 g) and evaporated. The crystals obtained (38.0 g; m.p. 150°-153° C.) are dissolved in boiling ethanol (520 cc). After 2 hours cooling at 2° C., the resulting crystals are separated by filtration, washed twice with ice-cold ethanol (total 80 cc) and dried under reduced pressure (0.1 mm.Hg) at 45° C. 4-Hydroxy-4-methyl-3-(6-methylpyrid-2-yl)-thiazolidine-2-thione (24.9 g), melting at 156° C., is obtained.

後処理

  1. filtrationAfter filtration and evaporation of the dimethylformamide under reduced pressure (0.1 mm.Hg) at 45° C.
  2. dissolutionthe residual oil is dissolved in ethyl acetate (500 cc)
  3. washthe organic solution is washed with distilled water (100 cc)
  4. dry with materialdried over sodium sulphate
  5. additiontreated with decolorising charcoal (2 g)
  6. customevaporated
  7. customThe crystals obtained (38.0 g; m.p. 150°-153° C.)
  8. dissolutionare dissolved
  9. customthe resulting crystals are separated by filtration
  10. washwashed twice with ice-cold ethanol (total 80 cc)
  11. customdried under reduced pressure (0.1 mm.Hg) at 45° C

出典と根拠

ORDレコード
ord-1b6f302e718a42a8827d125a22a0379b
出典データセット
uspto-grants-1979_08
特許番号
US04164579

反応ノート

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