Tributylphosphine → 5-[4-(1-Benzylbenzimidazol-5-ylmethoxy)benzyl]-3-triphenylmethylthiazolidine-2,4-dione

HRID 1419125노트

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HRID 1419125 반응식
[OH:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][CH:7]2[S:11][C:10](=[O:12])[N:9]([C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:8]2=[O:32])=[CH:4][CH:3]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC.[CH2:66]([N:73]1[C:77]2[CH:78]=[CH:79][C:80]([CH2:82]O)=[CH:81][C:76]=2[N:75]=[CH:74]1)[C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1>C1(C)C=CC=CC=1>[CH2:66]([N:73]1[C:77]2[CH:78]=[CH:79][C:80]([CH2:82][O:1][C:2]3[CH:3]=[CH:4][C:5]([CH2:6][CH:7]4[S:11][C:10](=[O:12])[N:9]([C:13]([C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=5)([C:14]5[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=5)[C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[C:8]4=[O:32])=[CH:33][CH:34]=3)=[CH:81][C:76]=2[N:75]=[CH:74]1)[C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1

참가 물질

6

반응물 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 28181265-(4-Hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dioneHCID 538271771-Benzyl-5-benzimidazolemethanol

생성물 1

HCID 867539805-[4-(1-Benzylbenzimidazol-5-ylmethoxy)benzyl]-3-triphenylmethylthiazolidine-2,4-dione수율 31.9%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of 822 mg of 5-(4-hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dione, 454 mg of azodicarbonyldipiperidine, 6 ml of dehydrated toluene and 0.44 ml of tributylphosphine was stirred for 30 minutes at room temperature. At the end of this time, 349 mg of 1-benzyl-5-benzimidazolemethanol were added to the reaction mixture and then the mixture was stirred for 3 hours, after which it was allowed to stand for 10 days at room temperature. The solvent was then removed by distillation under reduced pressure and the resulting residue was purified by column chromatography through silica gel using a gradient elution method, with mixtures of ethyl acetate and hexane in ratios ranging from 3:1 to 1:0 by volume as the eluent, to give 0.32 g of the title compound, softening at 90°-91° C.

후처리

  1. stirringthe mixture was stirred for 3 hours
  2. waitto stand for 10 days at room temperature
  3. customThe solvent was then removed by distillation under reduced pressure
  4. customthe resulting residue was purified by column chromatography through silica gel using
  5. washa gradient elution method

출처 및 근거

ORD 기록
ord-58aa5b54dfce4e29833e7293f1997554
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05886014

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