4-Methoxybenzaldehyde → 2-(4-Methoxyphenyl)-4,4,5,5-tetramethylimidazolidine-1,3-diol

HRID 531415Notes

Reaction equation

HRID 531415 reaction equation
[OH:1][NH:2][C:3]([CH3:10])([C:5]([NH:8][OH:9])([CH3:7])[CH3:6])[CH3:4].[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1>CO>[OH:1][N:2]1[C:3]([CH3:10])([CH3:4])[C:5]([CH3:7])([CH3:6])[N:8]([OH:9])[CH:17]1[C:16]1[CH:19]=[CH:20][C:13]([O:12][CH3:11])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 312444-MethoxybenzaldehydeHCID 844022,3-Butanediamine, N,N'-dihydroxy-2,3-dimethyl-

Product 1

HCID 591553772-(4-Methoxyphenyl)-4,4,5,5-tetramethylimidazolidine-1,3-diolYield 34%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,3-bis(hydroxylamino)-2,3-dimethylbutane (1.3 g, 8.8 mmol) and 4-methoxy-benzaldehyde (1.2 g, 8.8 mmol) in methanol (10 mL) was stirred at room temperature until reactants disappeared as TLC indicated. 1,3-Dihydroxy-2-(4-methoxyphenyl)-4,4,5,5-tetramethylimidazolidine was obtained by filtration, the filtrate was evaporated under reduced pressure to obtain the second crop of the title compound. The combined compound was then washed with petroleum ether and used for the next reaction (0.8 g, 34% yield). 1HNMR (400 MHz, DMSO): δ 7.63 (s, 1H), 7.32 (d, 1H, J=6.8), 6.87 (d, 1H, J=5.8), 4.42 (s, 1H), 3.72 (s, 3H), 1.06 (s, 3H), 1.02 (s, 3H).

Sources & evidence

ORD record
ord-ee17644a366a4f00ab689546353cea28
Source dataset
uspto-grants-2016_05
Patent number
US09353477B2

Reaction notes

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