p-Toluenesulfonic acid → 1,3-Bis-(4-fluorobenzoyl)benzene thiosemicarbazone

HRID 333204

反応式

HRID 333204 の反応式
[F:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14](=O)[C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[NH2:25][NH:26][C:27]([NH2:29])=[S:28].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[F:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14](=[N:25][NH:26][C:27]([NH2:29])=[S:28])[C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH:9]=2)=[O:7])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 6882631,3-Bis(4-fluorobenzoyl)benzeneHCID 2723789Thiosemicarbazide

生成物 1

HCID 781652501,3-Bis-(4-fluorobenzoyl)benzene thiosemicarbazone収率 52%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

1,3-bis-(4-fluorobenzoyl)benzene 12 (0.347 g, 1.08 mmol) was dissolved in anhydrous methanol (50 mL). The solution was heated at reflux for 15 min, and thiosemicarbazide (0.049 g, 0.54 mmol) and a catalytic amount of p-toluenesulfonic acid were added. After 10 h at reflux, the resulting solution was concentrated under reduced pressure. Purification using flash chromatography (silica gel, hexanes:ethyl acetate, 70:30) afforded the desired 1,3-bis-(4-fluorobenzoyl)benzene thiosemicarbazone (0.11 g, 0.278 mmol, 52% yield) as a white solid; 1H NMR (500 MHz, CDCl3): δ 8.67 (s, 1H, NH), 7.97 (m, 1H, ArH), 7.90 (m, 1H, ArH), 7.83 (m, 1H, ArH), 7.75 (m, 1H, ArH), 7.68 (m, 1H, ArH), 7.500 (m, 2H, ArH), 7.39 (s, 1H, NH2), 7.31 (m, 2H, ArH), 7.22 (ddd, J=8.5 Hz, 5.0 Hz, 3.0 Hz, 1H, ArH), 7.16 (ddd, J=8.5 Hz, 5.0 Hz, 3.0 Hz, 1H, ArH), 7.06 (ddd, J=8.5 Hz, 5.0 Hz, 3.0 Hz, 1H, ArH), 6.36 (s, 1H, NH2); HRMS (ESI) calculated for C21H15F2N3OSH (M+H)+ 396.0970, found 394.0834; HPLC retention time 13.740, 13.966 min.

後処理

  1. temperatureThe solution was heated
  2. temperatureat reflux for 15 min
  3. temperatureAfter 10 h at reflux
  4. concentrationthe resulting solution was concentrated under reduced pressure
  5. customPurification

出典と根拠

ORDレコード
ord-a10ef0d2f36843fa8a487e2296d36f7f
出典データセット
uspto-grants-2014_11
特許番号
US08877967B2

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