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

HRID 67695Notes

Reaction equation

HRID 67695 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]

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. customthe filtrate is evaporated to dryness under reduced pressure
  5. customThe residue is crystallised from acetonitrile and there

Sources & evidence

ORD record
ord-e2abee0271de4814bd345f12e3b0a54e
Source dataset
uspto-grants-1982_08
Patent number
US04346111

Reaction notes

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