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Sodium Azide → 5-(3-chlorophenyl)-alpha-(1-methyl-1H-imidazol-5-yl)-alpha-(4-methylphenyl)-tetrazolo[1,5-a]quinazoline-7-methanol

HRID 1441473
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HRID 1441473 반응식
Cl[C:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:19]([C:28]3[N:32]([CH3:33])[CH:31]=[N:30][CH:29]=3)([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)[OH:20])[CH:8]=2)[N:3]=1.[N-:34]=[N+:35]=[N-:36].[Na+]>CN(C=O)C>[Cl:18][C:14]1[CH:13]=[C:12]([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([C:19]([C:28]4[N:32]([CH3:33])[CH:31]=[N:30][CH:29]=4)([C:21]4[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=4)[OH:20])[CH:8]=3)[N:3]3[N:34]=[N:35][N:36]=[C:2]3[N:11]=2)[CH:17]=[CH:16][CH:15]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 33557Sodium AzideHCID 179761062-chloro-4-(3-chlorophenyl)-alpha-(1-methyl-1H-imidazol-5-yl)-alpha-(4-methylphenyl)-6-quinazolinemethanol

생성물 1

HCID 686877095-(3-chlorophenyl)-alpha-(1-methyl-1H-imidazol-5-yl)-alpha-(4-methylphenyl)-tetrazolo[1,5-a]quinazoline-7-methanol수율 72.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

A mixture of intermediate 24 (0.0105 mol) and sodium azide (0.031 mol) in DMF (70 ml) was stirred at 90° C. for 2 hours then cooled and poured out into ice water. The precipitate was filtered and taken up in DCM. The organic layer was washed with water, separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (15-40 μm) (eluent: DCM/MeOH/NH4OH; 95/5/0.1). The pure fractions were collected and the solvent was evaporated, yielding 3.68 g (quantitative) of 5-(3-chlorophenyl)-α-(1-methyl-1H-imidazol-5-yl)-α-(4-methylphenyl)-tetrazolo[1,5-a]quinazoline-7-methanol (intermediate 25), mp. 200° C.

후처리

  1. temperaturethen cooled
  2. filtrationThe precipitate was filtered
  3. washThe organic layer was washed with water
  4. customseparated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was purified by column chromatography over silica gel (15-40 μm) (eluent: DCM/MeOH/NH4OH; 95/5/0.1)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-61f19487dd8e40aab1e2b1437fdf0084
출처 데이터셋
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07655654B2

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