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

HRID 1845797Notes

Reaction equation

HRID 1845797 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-fd2cb89c47bd4815a409e6f444112bd5
Source dataset
uspto-grants-2015_02
Patent number
US08951766B2

Reaction notes

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