Lawesson's reagent → N-[5-Bromo-4-methyl-3-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-2-(4-methanesulfonyl-phenyl)-thioacetamide

HRID 1497761ノート

反応式

HRID 1497761 の反応式
[Br:1][C:2]1[C:3]([CH3:32])=[C:4]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[C:5]([NH:8][C:9](=O)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)=[N:6][CH:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:42])=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]([CH3:32])=[C:4]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[C:5]([NH:8][C:9](=[S:42])[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)=[N:6][CH:7]=1

参加物

4

反応物 2

HCID 87949Lawesson's reagent3 回HCID 86708096N-[5-Bromo-4-methyl-3-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-2-(4-methanesulfonyl-phenyl)-acetamide

生成物 1

HCID 86708097N-[5-Bromo-4-methyl-3-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-2-(4-methanesulfonyl-phenyl)-thioacetamide収率 60.7%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

To a suspension of N-[5-bromo-4-methyl-3-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-2-(4-methanesulfonyl-phenyl)-acetamide (Int. 10, 305 mg, 0.579 mmol) in toluene (15 mL) was added Lawesson's reagent (234 mg, 0.579 mmol) and the reaction mixture was heated at 110° C. for 24 hrs. A further amount of Lawesson's reagent (351 mg) was added and heating was continued for 2.5 hrs before a final addition of Lawesson's reagent (234 mg) was made. The reaction mixture was heated for 19 hrs then cooled, concentrated in vacuo and the resultant residue purified by flash chromatography eluting with a gradient of 0-50% ethyl acetate in cyclohexane to give the title compound as an orange glass (191 mg).

後処理

  1. temperatureheating
  2. temperatureThe reaction mixture was heated for 19 hrs
  3. temperaturethen cooled
  4. concentrationconcentrated in vacuo
  5. customthe resultant residue purified by flash chromatography
  6. washeluting with a gradient of 0-50% ethyl acetate in cyclohexane

出典と根拠

ORDレコード
ord-b674510928574ee0b674f10f2782c2b2
出典データセット
uspto-grants-2015_12
特許番号
US09199984B2

反応ノート

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