Sodium Nitrite → HCID 53655760, compound

HRID 2051799Notes

Reaction equation

HRID 2051799 reaction equation
[Cl:1][CH2:2][CH2:3][NH:4][C:5]([N:7]([CH:19]([CH3:21])[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:22]([O-])=[O:23].[Na+]>Cl>[Cl:1][CH2:2][CH2:3][N:4]([N:22]=[O:23])[C:5]([N:7]([CH:19]([CH3:21])[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 54461745HCID 54461745, compound

Product 1

HCID 53655760HCID 53655760, compoundYield 30.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

6.0 g of 1-(2-chloroethyl)-3-isopropyl-3-D-glucopyranosylurea are dissolved in 50 ml of 10% hydrochloric acid, and 6 g of sodium nitrite are added gradually thereto at 0° to 5° C. under stirring. The mixture is further stirred at the same temperature for 10 minutes. The reaction mixture is extracted with ethyl acetate. The extract is washed with an aqueous sodium bicarbonate solution, dried and evaporated to remove solvent. Then, the residue thus obtained is purified by silica gel chromatography (Solvent: chloroform-methanol(5:1)). 2.0 g of 1-(2-chloroethyl)-1-nitroso-3-isopropyl-3-D-glucopyranosylurea are thereby obtained as pale yellow caramel.

Workup

  1. stirringThe mixture is further stirred at the same temperature for 10 minutes
  2. extractionThe reaction mixture is extracted with ethyl acetate
  3. washThe extract is washed with an aqueous sodium bicarbonate solution
  4. customdried
  5. customevaporated
  6. customto remove solvent
  7. customThen, the residue thus obtained
  8. customis purified by silica gel chromatography (Solvent: chloroform-methanol(5:1))

Sources & evidence

ORD record
ord-f4e39ae3d1ac40d8bb641aff948813a9
Source dataset
uspto-grants-1980_01
Patent number
US04182757

Reaction notes

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