Ethylenediamine → p-Hydroxymethylbenzoylaminoethylamine acetate

HRID 2372514

Reaction equation

[OH:1][CH2:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9]CC)=[O:8])=[CH:5][CH:4]=1.[CH2:14]([NH2:17])[CH2:15][NH2:16]>>[C:7]([OH:9])(=[O:8])[CH3:6].[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:16][CH2:15][CH2:14][NH2:17])=[O:9])=[CH:12][CH:13]=1

Participants

Reactant 2

HCID 3301Ethylenediamine

HCID 12480307Ethyl 4-(hydroxymethyl)benzoate

Product 1

HCID 67918850p-Hydroxymethylbenzoylaminoethylamine acetateYield 49%

Procedure

Ethyl p- hydroxymethylbenzoate (0.51 g, 2.8 mmol) was dissolved in ethylene diamine and heated on a steam bath overnight. The volume was reduced under a stream of nitrogen and the residue was chromatographed by preparative thin layer chromatography (silica, CHCl3 : MeOH:HOAc, 10:10:1) to yield the product as an oil (0.35 g, 49% yield).

Workup

temperatureheated on a steam bath overnight
customthe residue was chromatographed by preparative thin layer chromatography (silica, CHCl3 : MeOH:HOAc, 10:10:1)

Sources & evidence

ORD record: ord-a191819783a74eb5b51fd002fccb8f73
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05098996

Linked notes

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