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

HRID 1419125Notes

Reaction equation

HRID 1419125 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-58aa5b54dfce4e29833e7293f1997554
Source dataset
uspto-grants-1999_03
Patent number
US05886014

Reaction notes

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