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

HRID 388190Notes

Reaction equation

HRID 388190 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, 1 H), 7.32 (d, 1 H, J=6.8), 6.87 (d, 1 H, J=5.8), 4.42 (s, 1 H), 3.72 (s, 3 H), 1.06 (s, 3 H), 1.02 (s, 3 H).

Sources & evidence

ORD record
ord-cf814bd6504a4b24a85bc4bff699061f
Source dataset
uspto-grants-2013_02
Patent number
US08377670B2

Reaction notes

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