Triphenylphosphine → 3-[3-(1-Triphenylmethyl-imidazol-4-yl)-propyl]-5-methyl-5-naphthalen-1-yl-imidazolidin-2,4-dione

HRID 1934812Notes

Reaction equation

HRID 1934812 reaction equation
[CH3:1][C:2]1([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][CH:10]=2)[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].[C:19]1([C:25]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:26]2[CH:30]=[C:29]([CH2:31][CH2:32][CH2:33]O)[N:28]=[CH:27]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:41]1([C:25]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[N:26]2[CH:30]=[C:29]([CH2:31][CH2:32][CH2:33][N:4]3[C:3](=[O:8])[C:2]([CH3:1])([C:9]4[C:18]5[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=5)[CH:12]=[CH:11][CH:10]=4)[NH:6][C:5]3=[O:7])[N:28]=[CH:27]2)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 2405155-Methyl-5-(naphthalen-1-yl)imidazolidine-2,4-dioneHCID 108328403-(1-Trityl-1H-imidazol-4-YL)propan-1-OL

Product 1

HCID 224668503-[3-(1-Triphenylmethyl-imidazol-4-yl)-propyl]-5-methyl-5-naphthalen-1-yl-imidazolidin-2,4-dioneYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.60 g(2.5 mmol) of 5-methyl-5-naphthalen-1-yl-imidazolidin-2,4-dione prepared in Preparation 1, 1.02 g(2.76 mmol) of 3-(1-triphenylmethyl-imidazol-4-yl)-propanol and 0.87 g(3.3 mmol) of triphenylphosphine (Ph3P) were dissolved in 50 ml of tetrahydrofuran. 0.52 ml(3.3 mmol) of diethylazodicarboxylate[DEAD] was added thereto and the resulting solution was stirred for 24 hours. Tetrahydrofuran was removed under reduced pressure and the residue was subjected to chromatography using ethyl acetate the eluent to obtain 1.17 g(Yield: 80%) of the title compound.

Workup

  1. customTetrahydrofuran was removed under reduced pressure

Sources & evidence

ORD record
ord-79a1f4b2a9b14750a3a80e5c5b531252
Source dataset
uspto-grants-2002_05
Patent number
US06384061B1

Reaction notes

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