Sodium Nitrite → HCID 54102119, compound

HRID 2083775Notes

Reaction equation

HRID 2083775 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C@@H:7]1[O:15][C@H:14]([CH2:16][OH:17])[C@@H:12]([OH:13])[C@H:10]([OH:11])[C@H:8]1[OH:9])=[O:5])[CH3:2].[N:18]([O-])=[O:19].[Na+]>O.C(O)(=O)C>[CH2:1]([N:3]([N:18]=[O:19])[C:4]([NH:6][C@@H:7]1[O:15][C@H:14]([CH2:16][OH:17])[C@@H:12]([OH:13])[C@H:10]([OH:11])[C@H:8]1[OH:9])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 54448322HCID 54448322, compound

Product 1

HCID 54102119HCID 54102119, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

1-ethyl-3-(β-D-glucopyranosyl)urea (930 mg) was dissolved in a mixture of water (4.3 ml) and acetic acid (4.3 ml), and to the solution was added 370 mg (1.5 mol. equivalents) of sodium nitrite in small portions under stirring. The mixture was stirred overnight at ambient temperature to complete the nitrosation. The reaction mixture was then treated with 4 ml of a cation-exchange resin, Amberlite IR-120 (H+ form), to remove the sodium ion therefrom. The reaction mixture was subsequently freeze-dried, affording 1.0 g of the titled compound as an amorphous substance of pale yellow color. [α]D26 -2° (c 1.0, H2O). This substance gave a single spot at Rf 0.82 in a thin layer chromatography on silica gel using chloroform-methanol (3:2 by volume) as eluent.

Workup

  1. stirringThe mixture was stirred overnight at ambient temperature
  2. customto remove the sodium ion
  3. customThe reaction mixture was subsequently freeze-dried

Sources & evidence

ORD record
ord-ec91b8fd2726427e8e14f3725f593536
Source dataset
uspto-grants-1978_04
Patent number
US04086415

Reaction notes

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