Trityl chloride → 4-(3-bromophenyl)-2-(triphenylmethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 70298

반응식

HRID 70298 반응식
[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[N:11][NH:10][C:9]2=[O:13])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Cl[C:17]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[N:11][N:10]([C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:9]2=[O:13])[CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 671603674-(3-bromophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

생성물 1

HCID 582766234-(3-bromophenyl)-2-(triphenylmethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 4-(3-bromophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (250 mg, 1.04 mmol) and NaH (50 mg of a 60% dispersion in mineral oil, 1.25 mmol) in DMF (3 mL) was stirred at room temperature for 30 min. To the solution was added 1,1′,1″-(chloromethanetriyl)tribenzene (305 mg, 1.09 mmol) and the mixture stirred at room temperature for 4 hr. The reaction mixture was diluted with EtOAc, washed with H2O and brine, dried over Na2SO4 then concentrated in vacu. The residue was purified by silica gel chromatography (EtOAc/Hexanes) to give 4-(3-bromophenyl)-2-(triphenylmethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one as a pale yellow foam. 1H NMR (400 MHz, DMSO-d6) δ 7.22-7.31 (m, 15 H), 7.40-7.42 (m, 1H), 7.51 (d, J=7.8 Hz, 1H), 7.63 (d, J=7.8 Hz, 1H), 7.90 (s, 1H), 8.60 (s, 1H).

후처리

  1. stirringthe mixture stirred at room temperature for 4 hr
  2. washwashed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. concentrationthen concentrated in vacu
  5. customThe residue was purified by silica gel chromatography (EtOAc/Hexanes)

출처 및 근거

ORD 기록
ord-0734f608f1114eb39f45df0a454ca0aa
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822518B2

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