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

HRID 2309687
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HRID 2309687 반응식
[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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 5504TolazolineHCID 11430Potassium CarbonateHCID 679672,4-Difluoronitrobenzene

생성물 1

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

시약·촉매·용매 1

HCID 3776Isopropanol용매

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온도
50 °C

실험 절차

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##

후처리

  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

출처 및 근거

ORD 기록
ord-657c238ee8d54bd9a75a8cb92122b09f
출처 데이터셋
uspto-grants-1987_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04696928

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