4-Chlorobenzoyl chloride → 5-(p-Chlorobenzoyl)-2-methoxycarbonyl-4-methylthio-1-methylpyrrole

HRID 1388926ノート

反応式

HRID 1388926 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:15][O:16][C:17]([C:19]1[N:20]([CH3:26])[CH:21]=[C:22]([S:24][CH3:25])[CH:23]=1)=[O:18]>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([C:21]2[N:20]([CH3:26])[C:19]([C:17]([O:16][CH3:15])=[O:18])=[CH:23][C:22]=2[S:24][CH3:25])=[O:7])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 85014-Chlorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 13345725Methyl 1-methyl-4-(methylsulfanyl)-1H-pyrrole-2-carboxylate

生成物 1

HCID 204690975-(p-Chlorobenzoyl)-2-methoxycarbonyl-4-methylthio-1-methylpyrrole収率 30.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

p-Chlorobenzoyl chloride (2.75 ml, 20 mmol), dissolved 20 ml of methylene chloride and 2.6 g (20 mmol) of aluminum chloride are mixed well at room temperature. After about 5 minutes 1.87 g (10 mmole) of 2-methoxycarbonyl-4-methylthio-1-methylpyrrole is added dropwise. The reaction mixture turns immediately into a dark red colored solution. The reaction is stirred for one hour before it is diluted with 75 ml of methylene chloride and extracted with water. The methylene chloride layer is separated, washed sucessively with 25 ml sodium bicarbonate solution and 50 ml of saturated brine, dried over anhydrous sodium sulfate and concentrated to an oil. The oil is crystallized from ethanol to give 1.0 g of 5-(p-chlorobenzoyl)-2-methoxycarbonyl-4-methylthio-1-methylpyrrole.

後処理

  1. additionare mixed well at room temperature
  2. extractionextracted with water
  3. customThe methylene chloride layer is separated
  4. washwashed sucessively with 25 ml sodium bicarbonate solution and 50 ml of saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated to an oil
  7. customThe oil is crystallized from ethanol

出典と根拠

ORDレコード
ord-233a0f9f588c4c8abfc04824658be01a
出典データセット
uspto-grants-1984_02
特許番号
US04434175

反応ノート

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