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

HRID 1388928노트

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HRID 1388928 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-90142828b06a435bb65a732e0f153a11
출처 데이터셋
uspto-grants-1984_02
특허 번호
US04434175

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