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Ethylenediamine → 2-{3-[(2-Aminoethyl)amino]-2-hydroxypropoxy}benzamide

HRID 904662
Notes
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Reaction equation

HRID 904662 reaction equation
[C:1]([C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[O:6][CH2:7][CH:8]1[O:10][CH2:9]1)(=[O:3])[NH2:2].[CH2:15]([NH2:18])[CH2:16][NH2:17]>>[C:1]([C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[O:6][CH2:7][CH:8]([OH:10])[CH2:9][NH:17][CH2:16][CH2:15][NH2:18])(=[O:3])[NH2:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 12548678HCID 12548678, compound

Product 1

HCID 204785302-{3-[(2-Aminoethyl)amino]-2-hydroxypropoxy}benzamide

Procedure

1-(o-Carbamoylphenoxy)-2,3-epoxypropane (20 g.) is added to ethylenediamine (125 ml.) and the mixture is stirred at laboratory temperature for 1 hour and then evaporated to dryness under reduced pressure. The residue is stirred with water (150 ml.), the mixture is filtered and the filtrate is evaporated to dryness under reduced pressure. The residue is crystallised from acetonitrile and there is thus obtained as residue 1-(o-carbamoylphenoxy)-3-(β-aminoethyl) aminopropan-2-ol, m.p. 91°-93° C.

Workup

  1. customevaporated to dryness under reduced pressure
  2. stirringThe residue is stirred with water (150 ml.)
  3. filtrationthe mixture is filtered
  4. custom
the filtrate is evaporated to dryness under reduced pressure
  • customThe residue is crystallised from acetonitrile and there
  • Sources & evidence

    ORD record
    ord-f385ef67cea64810935b80d855e47e3e
    Source dataset
    uspto-grants-1983_12
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US04419363

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes