Lawesson's reagent → 3-(3,5-Dichloro-benzenesulfonylamino)-4-methoxy-N-phenyl-thiobenzamide

HRID 1387596

반응식

HRID 1387596 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([NH:12][C:13]2[CH:14]=[C:15]([CH:25]=[CH:26][C:27]=2[O:28][CH3:29])[C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=O)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:39])=CC=1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([NH:12][C:13]2[CH:14]=[C:15]([CH:25]=[CH:26][C:27]=2[O:28][CH3:29])[C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[S:39])(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1

참가 물질

4

반응물 2

HCID 87949Lawesson's reagentHCID 98900163-(3,5-Dichloro-benzenesulfonylamino)-4-methoxy-N-phenyl-benzamide

생성물 1

HCID 99342723-(3,5-Dichloro-benzenesulfonylamino)-4-methoxy-N-phenyl-thiobenzamide수율 81.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

A mixture of 3-(3,5-dichloro-benzenesulfonylamino)-4-methoxy-N-phenyl-benzamide from Example 118 (3.61 g, 8.0 mmol) and Lawesson's reagent (3.57 g, 8.8 mmol) was stirred at room temperature overnight in tetrahydrofuran (250 mL). The reaction mixture was warmed to 50° C. for about one hour, then to 65° C. for about 4 hours then stirred at room temperature overnight. The mixture was concentrated to dryness and the residue dissolved in ethyl acetate and filtered through silica gel. Concentration of the eluant followed by trituration in hexanes/ethyl acetate (1:1) afforded the crude product (3.06 g). A portion (0.8 g) of this was chromatographed on silica gel in hexanes/ethyl acetate (1:1) to afford a pure sample (0.324 g); m.p. 206-208° C.

후처리

  1. concentrationThe mixture was concentrated to dryness
  2. dissolutionthe residue dissolved in ethyl acetate
  3. filtrationfiltered through silica gel

출처 및 근거

ORD 기록
ord-a1c4d9bf5c8647c4802bdc219ee282bc
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06268387B1

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