Sodium Nitrite → HCID 54066610, compound

HRID 1733259Notes

Reaction equation

HRID 1733259 reaction equation
[Cl:1][CH2:2][CH2:3][NH:4][C:5]([N:7]([CH2:19][CH:20]1[O:24][CH2:23][CH2:22][CH2:21]1)[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:25]([O-])=[O:26].[Na+]>C(O)=O>[Cl:1][CH2:2][CH2:3][N:4]([N:25]=[O:26])[C:5]([N:7]([CH2:19][CH:20]1[O:24][CH2:23][CH2:22][CH2:21]1)[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 54190173HCID 54190173, compound

Product 1

HCID 54066610HCID 54066610, compoundYield 22.6%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
0 °C

Procedure

3.7 g of 1-(2-chloroethyl)-3-tetrahydrofurfuryl-3-(D-galactopyranosyl)urea are dissolved in 15 ml of formic acid, and 2.1 g of sodium nitrite are added gradually thereto at 0° C. for one hour under stirring. The mixture is further stirred at the same temperature for 30 minutes. 100 ml of etherhexane (1:1) are added to the reaction mixture. The resultant oil is washed with ether. Then, 100 ml of ethyl acetate-methanol (10:1) 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: ethyl acetate-chloroform-methanol (5:2:1)). 0.9 g of 1-(2-chloroethyl)-1-nitroso-3-tetrahydrofurfuryl-3-(D-galactopyranosyl)urea are thereby obtained as yellow caramel.

Workup

  1. stirringThe mixture is further stirred at the same temperature for 30 minutes
  2. addition100 ml of etherhexane (1:1) are added to the reaction mixture
  3. washThe resultant oil is washed with ether
  4. additionThen, 100 ml of ethyl acetate-methanol (10:1) 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: ethyl acetate-chloroform-methanol (5:2:1))

Sources & evidence

ORD record
ord-da56d04e129c40b59a0f9ac8f8eafd40
Source dataset
uspto-grants-1980_12
Patent number
US04241052

Reaction notes

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