p-Toluenesulfonic acid → N-(4-chlorophenyl)-6-methyl-2,3-dihydro-1,4-dithiine-5-carboxamide

HRID 1938860

반응식

HRID 1938860 반응식
Cl[CH:2]([C:13](=O)[CH3:14])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)=[O:4].[CH2:16]([SH:19])[CH2:17][SH:18].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([NH:5][C:3]([C:2]2[S:18][CH2:17][CH2:16][S:19][C:13]=2[CH3:14])=[O:4])=[CH:7][CH:8]=1

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 109021,2-EthanedithiolHCID 27785032-chloro-N-(4-chlorophenyl)-3-oxobutanamide

생성물 1

HCID 470321N-(4-chlorophenyl)-6-methyl-2,3-dihydro-1,4-dithiine-5-carboxamide수율 84%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

2-Chloro-N-(4-chlorophenyl)-3-oxobutanamide (24.7 g, 0.1 mole), 1,2-ethanedithiol (9.4 g, 0.1 mole) and a small amount of p-toluenesulfonic acid were heated under reflux in benzene (150 ml), using a Dean-Stark trap to remove water (1.9 ml collected). The reaction mixture was filtered, treated with triethylamine (8 ml), and refluxed for a further 30 minutes. The mixture was then washed with water, dilute hydrochloric acid, and water. Evaporation of the benzene gave a white solid, which was recrystallized from absolute ethanol. The product melted at 115°-117° C. (24 g, 84% yield).

후처리

  1. customto remove water (1.9 ml collected)
  2. filtrationThe reaction mixture was filtered
  3. additiontreated with triethylamine (8 ml)
  4. temperaturerefluxed for a further 30 minutes
  5. washThe mixture was then washed with water, dilute hydrochloric acid, and water
  6. customEvaporation of the benzene
  7. customgave a white solid, which
  8. customwas recrystallized from absolute ethanol

출처 및 근거

ORD 기록
ord-dcc403132c184d519fb5affe5d90f5bf
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05693827

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