Methanol → tris(hydroxymethyl)methylammonium

HRID 414107Notes

Reaction equation

HRID 414107 reaction equation
[OH:1][C:2]1[CH2:6][N:5]([CH2:7][C:8]([NH2:10])=[O:9])[C:4](=[O:11])[C:3]=1[C:12]1[CH2:16][N:15]([CH2:17][C:18]([NH2:20])=[O:19])[C:14](=[O:21])[CH:13]=1.[OH:22][CH2:23]C(CO)(CO)N.C[OH:31]>>[OH:22][CH2:23][N+:15]([CH2:14][OH:21])([CH2:16][OH:31])[CH3:17].[OH:1][C:2]1[CH2:6][N:5]([CH2:7][C:8]([NH2:10])=[O:9])[C:4](=[O:11])[C:3]=1[C:12]1[CH2:16][N:15]([CH2:17][C:18]([NH2:20])=[O:19])[C:14](=[O:21])[CH:13]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6503Tris(hydroxymethyl)aminomethaneHCID 54680446HCID 54680446, compound

Product 2

HCID 4468930tris(hydroxymethyl)methylammoniumHCID 54680446HCID 54680446, compound

Procedure

3.0 g (0.010 mol) of 1,1',5,5'-tetrahydro-4-hydroxy-2,2'-dioxo-[3,4'-bi-2H-pyrrole]-1,1'-diacetic acid diamide are suspended in 70 ml of methanol; 2.4 g of tris-(hydroxymethyl)-aminomethane are added and the whole is stirred at room temperature for 12 hours, during which time the free acid goes into solution and precipitates again in the form of a salt. The resulting precipitate is filtered off, washed with cold methanol and dried under greatly reduced pressure at 60°. The tris-(hydroxymethyl)-methylammonium salt of 1,1',5,5'-tetrahydro-4-hydroxy-2,2'-dioxo-[3,4'-bi-2H-pyrrole]-1,1'-diacetic acid diamide is obtained in the form of white crystals having a melting point of 203° (decomposition).

Workup

  1. customprecipitates again in the form of a salt
  2. filtrationThe resulting precipitate is filtered off
  3. washwashed with cold methanol
  4. customdried under greatly reduced pressure at 60°

Sources & evidence

ORD record
ord-9a02793f37b64e8ea87c811990e5872f
Source dataset
uspto-grants-1988_12
Patent number
US04789674

Reaction notes

Loading…