Nitronium tetrafluoroborate → 1-(7-Hydroxy-6-nitro-2-benzothiazolyl)-3-ethyl-urea

HRID 9118

反応式

HRID 9118 の反応式
F[B-](F)(F)F.[O:6]=[N+:7]=[O:8].[OH:9][C:10]1[C:18]2[S:17][C:16]([NH:19][C:20]([NH:22][CH2:23][CH3:24])=[O:21])=[N:15][C:14]=2[CH:13]=[CH:12][CH:11]=1>C(#N)C.C(OCC)C>[OH:9][C:10]1[C:18]2[S:17][C:16]([NH:19][C:20]([NH:22][CH2:23][CH3:24])=[O:21])=[N:15][C:14]=2[CH:13]=[CH:12][C:11]=1[N+:7]([O-:8])=[O:6]

参加物

5

反応物 2

HCID 11073463Nitronium tetrafluoroborateHCID 219855231-(7-Hydroxy-2-benzothiazolyl)-3-ethyl-urea

生成物 1

HCID 219856421-(7-Hydroxy-6-nitro-2-benzothiazolyl)-3-ethyl-urea収率 10.4%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6342Acetonitrile溶媒2 回

反応条件

温度
20 °C

実験手順

To a solution of 2-methylpyridone (0.020 mL, 0.20 mmol, 1.2 eq) in anhydrous acetonitrile (0.5 mL), nitronium tetrafluoroborate (0.045 g, 0.32 mmol, 1.9 eq) was added. The suspension was stirred at about 20° C. for about 5 minutes to get an orange solution. The solution was then transferred to a suspension of 1-(7-hydroxy-2-benzothiazolyl)-3-ethyl-urea 8 (0.040 g, 0.17 mmol) in acetonitrile (0.5 mL). The reaction mixture was stirred at about 20° C. for about 15 minutes, then taken up in diethyl ether (8 mL), and neutralized by washing with saturated sodium bicarbonate solution (1.5 mL). The organic extract was concentrated and dissolved in methanol (2 mL). LC/MS purification was followed by flash chromatography purification on silica (methylene chloride/methanol=40/1) to afford 0.005 g (10%) of the desired compound 17. 1H NMR (DMSO) δ 11.20 (br s, 1H, NH), 8.02 (d, 1H, J=9.0 Hz, ArH), 7.23 (d, 1H, J=7.5 Hz, ArH), 6.78 (br s, 1H, NH), 3.20 (m, 2H, CH2), 1.10 (t, 3H, J=7.2 Hz, CH3). LC/MS 283 (MH+); RP-HPLC RT 2.74 minutes.

後処理

  1. customto get an orange solution
  2. stirringThe reaction mixture was stirred at about 20° C. for about 15 minutes
  3. washby washing with saturated sodium bicarbonate solution (1.5 mL)
  4. extractionThe organic extract
  5. concentrationwas concentrated
  6. dissolutiondissolved in methanol (2 mL)
  7. customLC/MS purification
  8. customwas followed by flash chromatography purification on silica (methylene chloride/methanol=40/1)

出典と根拠

ORDレコード
ord-c336b764197e420a978d946859501796
出典データセット
uspto-grants-2006_08
特許番号
US07091227B2

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