Dimethyl Sulfoxide → alpha-(alpha,alpha-Dimethyl-2,3,4-trimethoxyphenethylimino)-2-methoxyacetophenone

HRID 1680887Notes

Reaction equation

[CH3:1][C:2]([NH2:17])([CH3:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[C:5]=1[O:14][CH3:15].O.CO[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]([CH:29]=[O:30])=[O:28].[CH3:31]S(C)=O>>[CH3:16][C:2]([N:17]=[C:29]([O:30][CH3:31])[C:27]([C:22]1[CH:21]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:28])([CH3:1])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[C:5]=1[O:14][CH3:15]

Participants

Reactant 3

HCID 679Dimethyl Sulfoxide2×

HCID 130205972-Methyl-1-(2,3,4-trimethoxyphenyl)propan-2-amine

HCID 204341102-Methoxyphenylglyoxal hydrate

Product 1

HCID 23454833alpha-(alpha,alpha-Dimethyl-2,3,4-trimethoxyphenethylimino)-2-methoxyacetophenone

Conditions

Temperature: 20 °C

Procedure

A solution of 133 mg of α,α-dimethyl-2,3,4-trimethoxyphenethylamine in 1.5 ml of dimethylsulfoxide is added to 111 mg of 2-methoxyphenylglyoxal hydrate, and the mixture is stirred at 20° C. for one hour, whereby a solution of α-(α,α-dimethyl-2,3,4-trimethoxyphenethylimino)-2-methoxyacetophenone in dimethylsulfoxide is obtained.

Sources & evidence

ORD record: ord-d9c89c4dfa1c4c26bef4105832ba69f9
Source dataset: uspto-grants-1981_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04276304

Reaction notes

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