Phosphorus oxychloride → 2-(Methylthio)-5-(4-fluorobenzoyl)pyrrole

HRID 1262953

反応式

HRID 1262953 の反応式
CN(C)[C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1.P(Cl)(Cl)(Cl)=O.[CH3:18][S:19][C:20]1[NH:21][CH:22]=[CH:23][CH:24]=1.C([O-])(=O)C.[Na+]>ClCCCl.O>[CH3:18][S:19][C:20]1[NH:21][C:22]([C:3](=[O:11])[C:4]2[CH:5]=[CH:6][C:7]([F:10])=[CH:8][CH:9]=2)=[CH:23][CH:24]=1

参加物

7

反応物 4

HCID 24813Phosphorus oxychlorideHCID 1410774-fluoro-N,N-dimethylbenzamideHCID 517045Sodium AcetateHCID 110078572-Methylthiopyrrole

生成物 1

HCID 129159012-(Methylthio)-5-(4-fluorobenzoyl)pyrrole収率 54.4%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 962Water溶媒

実験手順

A solution of N,N-dimethyl-4-fluorobenzamide (8.4 g, 0.05 moles) in anhydrous 1,2-dichloroethane (170 ml) containing phosphorus oxychloride (7.7 g, 0.05 moles) was heated at reflux temperature for 1 hour. At the end of this time 2-methylthiopyrrole (2.82 g, 0.025 moles) was added and heating was continued for an additional 0.5 hour. The solution was cooled to room temperature, and to the cooled solution was cautiously added, with good agitation, a solution of sodium acetate (12.3 g, 0.15 moles) in water (50 ml) and the mixture was then boiled under reflux for 1 hour. The organic phase was separated, washed with water, dried, and evaporated. The residue was subjected to column chromatography on silica gel suing ethyl acetate-hexane (1:9) as the eluting solvent. A yellow colored solid 2-(methylthio)-5-(4-fluorobenzoyl)pyrrole (3.2 g, 54%) was obtained which after crystallization from ether-hexane had m.p. 112°-113° C.

後処理

  1. temperaturewas heated
  2. temperatureat reflux temperature for 1 hour
  3. temperatureheating
  4. additionto the cooled solution was cautiously added, with good agitation
  5. temperatureunder reflux for 1 hour
  6. customThe organic phase was separated
  7. washwashed with water
  8. customdried
  9. customevaporated

出典と根拠

ORDレコード
ord-9684d184876247e4b2191db1b2ad4b80
出典データセット
uspto-grants-1984_06
特許番号
US04454326

関連ノート

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