Urea → 2-Hydroxy-5-[1-hydroxy-2-[(1,1-dimethyl-2-p-hydroxyphenylethyl)amino]-ethyl]benzeneacetonitrile

HRID 973247Notes

Reaction equation

OC1C=CC(NC(C)(C)C)=CC=1.C1(NC(C)(C)C)C=CC=CC=1.NC(N)=O.[CH3:28][C:29]([NH:39][CH2:40][C:41]([C:43]1[CH:44]=[CH:45][C:46]([OH:52])=[C:47]([CH2:49][C:50]#[N:51])[CH:48]=1)=[O:42])([CH3:38])[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=1>>[OH:52][C:46]1[CH:45]=[CH:44][C:43]([CH:41]([OH:42])[CH2:40][NH:39][C:29]([CH3:38])([CH3:28])[CH2:30][C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)=[CH:48][C:47]=1[CH2:49][C:50]#[N:51]

Participants

Reactant 4

HCID 1176Urea

HCID 254260N-(1,1-Dimethylethyl)benzenamine

HCID 21325158p-Hydroxyphenyl-t-butylamine

HCID 540672315-[N-(1,1-dimethyl-2-p-hydroxyphenylethyl)glycyl]-2-hydroxyphenylacetonitrile

Product 1

HCID 213251522-Hydroxy-5-[1-hydroxy-2-[(1,1-dimethyl-2-p-hydroxyphenylethyl)amino]-ethyl]benzeneacetonitrile

Procedure

The procedure of Example 1(c) is repeated with substitution of an equimolar amount of p-hydroxyphenyl-t-butylamine for phenyl-t-butylamine in that example. The resulting aminoketone, 5-[N-(1,1-dimethyl-2-p-hydroxyphenylethyl)glycyl]-2-hydroxyphenylacetonitrile, is reduced according to the procedure of Example 1(d) to yield 2-hydroxy-5-[1-hydroxy-2-[(1,1-dimethyl-2-p-hydroxyphenylethyl)amino]-ethyl]benzeneacetonitrile.

Sources & evidence

ORD record: ord-d26fa9b5d83e4d2fa8401c86454d56a0
Source dataset: uspto-grants-1977_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04055658

Reaction notes

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