Dimethylformamide → 5-(p-Chlorobenzoyl)-2-diazomethylcarbonyl-4-methylthio-1-methylpyrrole

HRID 1388928ノート

反応式

HRID 1388928 の反応式
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([C:14]([OH:16])=O)=[CH:10][C:9]=2[S:17][CH3:18])=[O:7])=[CH:4][CH:3]=1.C(Cl)(C(Cl)=O)=O.CN(C)C=O.[N+:32](=[CH2:34])=[N-:33]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([C:14]([CH:34]=[N+:32]=[N-:33])=[O:16])=[CH:10][C:9]=2[S:17][CH3:18])=[O:7])=[CH:19][CH:20]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 9550DiazomethaneHCID 65578Oxalyl chlorideHCID 204690825-(p-Chlorobenzoyl)-2-hydroxycarbonyl-4-methylthio-1-methylpyrrole

生成物 1

HCID 538466435-(p-Chlorobenzoyl)-2-diazomethylcarbonyl-4-methylthio-1-methylpyrrole

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of the crude 5-(p-chlorobenzoyl)-2-hydroxycarbonyl-4-methylthio-1-methylpyrrole in 3 ml of methylene chloride is added 100 μl of (COCl)2 followed by the addition of 0.5 μl of dimethylformamide (DMF). The resulting reaction mixture is stirred for about an hour and then concentrated to give a yellow solid. Subsequently freshly prepared diazomethane is added dropwise to a stirred solution of the yellow solid in 1 ml of methylene chloride at 0°. The reaction is allowed to warm up to room temperature over a period of one hour. After the excess amount of diazomethane is removed by bubbling nitrogen through the reaction mixture, the solvents are removed by evaporation under reduced pressure and a bright yellow solid is collected. This crude product, i.e., 5-(p-chlorobenzoyl)-2-diazomethylcarbonyl-4-methylthio-1-methylpyrrole, is used directly in the next step without further purification.

後処理

  1. customThe resulting reaction mixture
  2. concentrationconcentrated
  3. customto give a yellow solid
  4. customAfter the excess amount of diazomethane is removed
  5. customby bubbling nitrogen through the reaction mixture
  6. customthe solvents are removed by evaporation under reduced pressure
  7. customa bright yellow solid is collected
  8. customThis crude product, i.e., 5-(p-chlorobenzoyl)-2-diazomethylcarbonyl-4-methylthio-1-methylpyrrole, is used directly in the next step without further purification

出典と根拠

ORDレコード
ord-90142828b06a435bb65a732e0f153a11
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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