Sodium Nitrite → HCID 13092720, compound

HRID 2051793Notes

Reaction equation

HRID 2051793 reaction equation
[Cl:1][CH2:2][CH2:3][NH:4][C:5]([N:7]([CH2:19][CH3:20])[CH:8]1[O:16][C@H:15]([CH2:17][OH:18])[C@@H:13]([OH:14])[C@H:11]([OH:12])[C@H:9]1[OH:10])=[O:6].[N:21]([O-])=[O:22].[Na+]>C(O)=O>[Cl:1][CH2:2][CH2:3][N:4]([N:21]=[O:22])[C:5]([N:7]([CH2:19][CH3:20])[CH:8]1[O:16][C@H:15]([CH2:17][OH:18])[C@@H:13]([OH:14])[C@H:11]([OH:12])[C@H:9]1[OH:10])=[O:6]

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 53815364HCID 53815364, compound

Product 1

HCID 13092720HCID 13092720, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

6.0 g of 1-(2-chloroethyl)-3-ethyl-3-D-glucopyranosylurea are dissolved in 15 ml of formic acid, and 4.0 g of sodium nitrite are added gradually thereto at 0° to 5° C. for one hour under stirring. The mixture is further stirred at the same temperature for 20 minutes. 100 ml of ether-hexane(1:1) are added to the reaction mixture, and the resultant oil is collected therefrom. Said oil is washed with ether. Then, 100 ml of methylene chloride-methanol(5:1) are added to said oil, and insoluble materials are removed by filtration. The filtrate is evaporated to remove solvent, and the residue obtained is purified by silica gel chromatography (Solvent: chloroform-ethyl acetate-methanol (2:1:1)). 2.0 g of 1-(2-chloroethyl)-1-nitroso-3-ethyl-3-D-glucopyranosylurea are thereby obtained as pale yellow caramel.

Workup

  1. stirringThe mixture is further stirred at the same temperature for 20 minutes
  2. customthe resultant oil is collected
  3. washis washed with ether
  4. additionThen, 100 ml of methylene chloride-methanol(5:1) are added
  5. customare removed by filtration
  6. customThe filtrate is evaporated
  7. customto remove solvent
  8. customthe residue obtained
  9. customis purified by silica gel chromatography (Solvent: chloroform-ethyl acetate-methanol (2:1:1))

Sources & evidence

ORD record
ord-26ede358d54542d1b69a8c1534a80070
Source dataset
uspto-grants-1980_01
Patent number
US04182757

Reaction notes

Loading…