Ethanolamine → Ethanediamide, N1,N2-bis(2-hydroxyethyl)-

HRID 703245Notes

Reaction equation

HRID 703245 reaction equation
C(N[C:5]([C:7]([NH:9][C:10](=[O:12])[CH3:11])=O)=[O:6])(=O)C.[CH2:13]([CH2:15][NH2:16])[OH:14].C[OH:18]>>[OH:14][CH2:13][CH2:15][NH:16][C:11]([C:10]([NH:9][CH2:7][CH2:5][OH:6])=[O:12])=[O:18]

Participants

4

Reactant 3

HCID 700EthanolamineHCID 887Methanol2×HCID 3016168N,N'-Diacetyloxamide

Product 1

HCID 74638Ethanediamide, N1,N2-bis(2-hydroxyethyl)-Yield 93%

Procedure

A suspension of N,N'-diacetyloxamide (10 g, 0.058 mol) in anhydrous methyl alcohol (50 ml) is charged into a four-necked flask equipped with a reflux condenser, an inlet tube for nitrogen, a dropping funnel, a thermometer, and a magnetic stirrer. A solution of monoethanolamine (8.2 g, 0.134 mol) in anhydrous methyl alcohol (20 ml) is gradually dripped in at 25° C. The reaction is exothermic and the temperature rises up to 60° C. The reaction is allowed to proceed at this temperature for 2 hours, then the reaction mixture is cooled and the precipitate is recovered by filtration. The compound of the title is thus obtained (9.5 g, 0.054 mol, 93% yield) with m.p. 166°-69° C.

Workup

  1. additionis charged into a four-necked flask
  2. customequipped with a reflux condenser, an inlet tube for nitrogen, a dropping funnel
  3. customis gradually dripped in at 25° C
  4. customrises up to 60° C
  5. temperaturethe reaction mixture is cooled
  6. filtrationthe precipitate is recovered by filtration
  7. customThe compound of the title is thus obtained (9.5 g, 0.054 mol, 93% yield) with m.p. 166°-69° C.

Sources & evidence

ORD record
ord-7f5e065158ca4ef598b99bc1496d2865
Source dataset
uspto-grants-1991_01
Patent number
US04981963

Reaction notes

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