Sodium Nitrite → HCID 13092708, compound

HRID 2051790Notes

Reaction equation

HRID 2051790 reaction equation
[Cl:1][CH2:2][CH2:3][NH:4][C:5]([N:7]([CH3:19])[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:20]([O-])=[O:21].[Na+]>C(O)=O>[Cl:1][CH2:2][CH2:3][N:4]([N:20]=[O:21])[C:5]([N:7]([CH3:19])[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 54470639HCID 54470639, compound

Product 1

HCID 13092708HCID 13092708, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

1.2 g of 1-(2-chloroethyl)-3-methyl-3-D-glucopyranosylurea are dissolved in 10 ml of formic acid, and 0.56 g of sodium nitrite is added thereto at 0° to 5° C. for one hour under stirring. The mixture is further stirred at the same temperature for 1.5 hours. After the reaction, the mixture is freeze-dried. The residue thus obtained is purified by silica gel chromatography(Solvent: chloroform-ethyl acetate-methanol(2:1:1)). 0.6 g of 1-(2-chloroethyl)-1-nitroso-3-methyl-3-D-glucopyranosylurea is thereby obtained as a pale yellow powder.

Workup

  1. stirringThe mixture is further stirred at the same temperature for 1.5 hours
  2. customAfter the reaction
  3. customthe mixture is freeze-dried
  4. customThe residue thus obtained
  5. customis purified by silica gel chromatography(Solvent

Sources & evidence

ORD record
ord-0774a7c1e8f84620ac7545a72dbfd2a2
Source dataset
uspto-grants-1980_01
Patent number
US04182757

Reaction notes

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