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

HRID 1462050

반응식

HRID 1462050 반응식
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

참가 물질

7

반응물 4

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

생성물 1

HCID 129159012-(Methylthio)-5-(4-fluorobenzoyl)pyrrole수율 54.4%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 962Water용매

실험 절차

A solution of N,N-dimethyl-4-fluorobenzamide (8.4 g, 0.05 moles) in anhydrous 1,2-dichloroethane (170 ml) containing phosphorous 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.

후처리

  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

출처 및 근거

ORD 기록
ord-edb1536751c348f5ab93ce525c913a46
출처 데이터셋
uspto-grants-1984_07
특허 번호
US04458081

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