Pyridine → 3-n-Butyl-5-(4-cyanobenzyl) hydantoin

Reaction equation

FC(F)(F)C([NH:5]OC(=O)C(F)(F)F)=O.N1C=CC=CC=1.[CH2:21]([N:25]1[C:29](=[O:30])[CH:28]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([CH:38]=O)=[CH:34][CH:33]=2)[NH:27][C:26]1=[O:40])[CH2:22][CH2:23][CH3:24]>C1C=CC=CC=1>[CH2:21]([N:25]1[C:29](=[O:30])[CH:28]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]#[N:5])=[CH:34][CH:33]=2)[NH:27][C:26]1=[O:40])[CH2:22][CH2:23][CH3:24]

Participants

Procedure

The formyl compound (4.3 g., 0.01 mole), N,O-bis (trifluoroacetyl)hydroxylamine (3.6 g., 0.016 mole) and dry pyridine (2.6 ml. 0.032 mole) were mixed in benzene (75 ml) and heated under reflux for 2 hours. After cooling the benzene solution was washed with water (2×50 ml), dried over magnesium sulphate monohydrate and evaporated in vacuo to give an oil which slowly crystallised. This product was further purified by silica gel chromatography and recrystallisation from a small volume of ethyl acetate to give the title compound, yield 2.5 g., m.p. 136° C.