Triphenylphosphine → N-[4-(3-benzyl-2,4,5-trioxo-imidazolidin-1-yl)-butyl]-3-pyridin-3-yl-acrylamide

HRID 458871Notes

Reaction equation

HRID 458871 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:16])[CH:8]=[CH:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:36]([N:43]1[C:47](=[O:48])[C:46](=[O:49])[NH:45][C:44]1=[O:50])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(OC(N=NC(OCC)=O)=O)C>C1COCC1>[CH2:36]([N:43]1[C:47](=[O:48])[C:46](=[O:49])[N:45]([CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:16])[CH:8]=[CH:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[C:44]1=[O:50])[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5626191-Benzylimidazolidine-2,4,5-trioneHCID 53817888N-(4-hydroxybutyl)-3-pyridin-3-yl-acrylamide

Product 1

HCID 53673377N-[4-(3-benzyl-2,4,5-trioxo-imidazolidin-1-yl)-butyl]-3-pyridin-3-yl-acrylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Batch size: 4.4 g (20.0 mmol) N-(4-hydroxybutyl)-3-pyridin-3-yl-acrylamide, 5.2 g (19.8 mmol) triphenylphosphine, 4.1 g (20.1 mmol) 3-benzyl-2,4,5-trioxo-imidazolidine (production according to Ishii et al., J. Med. Chem. 39, 1924 (1996)) and 3.5 g (20.0 mmol) azodicarboxylic acid diethyl ester in 60 ml THF.

Sources & evidence

ORD record
ord-0f0dffb5a45d4e0ab6bb87c3e9cc8092
Source dataset
uspto-grants-2007_03
Patent number
US07192967B1

Reaction notes

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