Butyl iodide → 4-Butoxycarbonyl-5-(pyrazin-2-yl)-1,2-dithiole-3-thione

HRID 1390314ノート

反応式

HRID 1390314 の反応式
CN(P(N(C)C)(N(C)C)=O)C.[C:12]([C:15]1[C:16](=[S:26])[S:17][S:18][C:19]=1[C:20]1[CH:25]=[N:24][CH:23]=[CH:22][N:21]=1)([OH:14])=[O:13].[O-]CC.[Na+].[CH2:31](I)[CH2:32][CH2:33][CH3:34]>C(O)C.C(OCC)(=O)C>[CH2:31]([O:13][C:12]([C:15]1[C:16](=[S:26])[S:17][S:18][C:19]=1[C:20]1[CH:25]=[N:24][CH:23]=[CH:22][N:21]=1)=[O:14])[CH2:32][CH2:33][CH3:34]

参加物

7

反応物 4

HCID 10962Butyl iodideHCID 12679HexamethylphosphoramideHCID 2723922Sodium ethoxideHCID 213291664-Carboxy-5-(pyrazin-2-yl)-1,2-dithiole-3-thione

生成物 1

HCID 213291754-Butoxycarbonyl-5-(pyrazin-2-yl)-1,2-dithiole-3-thione収率 25.6%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

Anhydrous hexamethylphosphotriamide (5 cc) and 4-carboxy-5-(pyrazin-2-yl)-1,2-dithiole-3-thione (1.28 g) (prepared as described in Example 32) are added to a solution of dry sodium ethoxide (0.34 g) in anhydrous ethanol (5 cc). The suspension obtained is heated to a temperature of about 50° C., the resulting solution is cooled to a temperature of about 20° C. and then butyl iodide (1.7 g) is added. The reaction mixture is then maintained at a temperature of about 50° C. for 7 hours. An insoluble material is filtered off and the filtrate is evaporated to dryness under reduced pressure (20 mm Hg). The oil obtained is treated with ethyl acetate (2 cc) and the product which crystallises is filtered off and washed with diethyl ether (2 cc). After drying, 4-butoxycarbonyl-5-(pyrazin-2-yl)-1,2-dithiole-3-thione (0.4 g), melting at 127° C., is obtained.

後処理

  1. customThe suspension obtained
  2. temperaturethe resulting solution is cooled to a temperature of about 20° C.
  3. temperatureThe reaction mixture is then maintained at a temperature of about 50° C. for 7 hours
  4. filtrationAn insoluble material is filtered off
  5. customthe filtrate is evaporated to dryness under reduced pressure (20 mm Hg)
  6. customThe oil obtained
  7. customthe product which crystallises
  8. filtrationis filtered off
  9. washwashed with diethyl ether (2 cc)
  10. customAfter drying

出典と根拠

ORDレコード
ord-b84680be841a40f181ffa43cf38a626c
出典データセット
uspto-grants-1979_02
特許番号
US04138487

反応ノート

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