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Tolazoline → 1,2-Dihydro-8-fluoro-4-phenylimidazo[1,2-a]quinoxaline 5-oxide

HRID 2309687
ノート
印刷プレビュー

反応式

HRID 2309687 の反応式
[CH:1]1[CH:2]=[CH:3][C:4]([CH2:7][C:8]2[NH:12][CH2:11][CH2:10][N:9]=2)=[CH:5][CH:6]=1.F[C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[N+:21]([O-])=[O:22].C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C>[F:20][C:18]1[CH:19]=[C:14]2[C:15]([N+:21]([O-:22])=[C:7]([C:4]3[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=3)[C:8]3[N:9]2[CH2:10][CH2:11][N:12]=3)=[CH:16][CH:17]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 5504TolazolineHCID 11430Potassium CarbonateHCID 679672,4-Difluoronitrobenzene

生成物 1

HCID 139586071,2-Dihydro-8-fluoro-4-phenylimidazo[1,2-a]quinoxaline 5-oxide収率 54.7%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
50 °C

実験手順

A mixture of tolazoline (40 g, 0.25 mol), 2,4-difluoronitrobenzene (39.75 g, 0.25 mol) and potassium carbonate (17.26 g, 0.125 mol) in isopropanol (500 ml) was heated to 50° C. for a period of two days. The solvent was removed in vacuo from the mixture and the residue was dissolved in dichloromethane. The resulting solution was filtered and the solvent removed in vacuo to yield a yellow solid which was chromatographed on silica gel using 2% methanol/chloroform as the eluent to yield 1,2-dihydro-8-fluoro-4-phenylimidazo[1,2-a]quinoxaline 5-oxide (38.5 g) as an orange solid, having a m.p. 188°-193° C., (Found: C, 68.07; H 4.23; N 14.82%; C16H12FN3O requires C 68.33; H 4.27; N 14.95%) and represented by the structural formula ##STR14##

後処理

  1. customThe solvent was removed in vacuo from the mixture
  2. dissolutionthe residue was dissolved in dichloromethane
  3. filtrationThe resulting solution was filtered
  4. customthe solvent removed in vacuo
  5. customto yield a yellow solid which
  6. customwas chromatographed on silica gel using 2% methanol/chloroform as the eluent

出典と根拠

ORDレコード
ord-657c238ee8d54bd9a75a8cb92122b09f
出典データセット
uspto-grants-1987_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04696928

反応ノート

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