Tributylphosphine → HCID 86758454, compound

HRID 2303912Notes

Reaction equation

HRID 2303912 reaction equation
[C:1]([C:3]1[CH:21]=[CH:20][C:6]([O:7][C:8]2[C:16]3[N:15]=[C:14]([CH2:17][OH:18])[N:13]([CH3:19])[C:12]=3[CH:11]=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)#[N:2].O[C:23]1[CH:55]=[CH:54][C:26]([CH2:27][CH:28]2[S:32][C:31](=[O:33])[N:30]([C:34]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:29]2=[O:53])=[CH:25][CH:24]=1.C(P(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:21]=[CH:20][C:6]([O:7][C:8]2[CH:9]=[CH:10][C:11]3[N:15]=[C:14]([CH2:17][O:18][C:23]4[CH:55]=[CH:54][C:26]([CH2:27][CH:28]5[S:32][C:31](=[O:33])[N:30]([C:34]([C:47]6[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=6)([C:41]6[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=6)[C:35]6[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=6)[C:29]5=[O:53])=[CH:25][CH:24]=4)[N:13]([CH3:19])[C:12]=3[CH:16]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 28181265-(4-Hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dioneHCID 18461474HCID 18461474, compound

Product 1

HCID 86758454HCID 86758454, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-cyanophenoxy-2-hydroxymethyl-1-methyl-1H-benzimidazole (279 mg), 5-(4-hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dione (558 mg), azodicarbonylpiperidine (378 mg), tri-n-butylphosphine (303 mg) and toluene (20 ml) was stirred at ambient temperature for 15 hours. The reaction mixture was purified by chromatography on a silica gel column using n-hexane/ethyl acetate=1/1 as the eluant to give the title compound (706 mg).

Workup

  1. customThe reaction mixture was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-cf7c821a484f4e8e9236b4ced939cbe5
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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