Methanol → HCID 13092717, compound

HRID 2051796Notes

Reaction equation

HRID 2051796 reaction equation
[Cl:1][CH2:2][CH2:3][NH:4][C:5]([N:7]([CH2:19][CH2:20][CH3:21])[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+].CO.C(=O)([O-])[O-].[K+].[K+]>C(O)=O.C(OCC)(=O)C>[Cl:1][CH2:2][CH2:3][N:4]([N:22]=[O:23])[C:5]([N:7]([CH2:19][CH2:20][CH3:21])[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

7

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 23668193Sodium NitriteHCID 54055121HCID 54055121, compound

Product 1

HCID 13092717HCID 13092717, compoundYield 30.6%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

4.5 g of 1-(2-chloroethyl)-3-n-propyl-3-D-glucopyranosylurea are dissolved in 20 ml of formic acid, and 2.8 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 one hour. After the reaction, 20 ml of methanol are added to the reaction mixture. Said mixture is neutralized with potassium carbonate under ice-cooling. Then, 150 ml of ethyl acetate are added to said mixture, and insoluble materials are removed by filtration. The filtrate is washed with an aqueous sodium bicarbonate solution, dried and evaporated to remove solvent. The residue thus obtained is purified by silica gel chromatography(Solvent: methanol-chloroform(1:5)). 1.5 g of 1-(2-chloroethyl)-1-nitroso-3-n-propyl-3-D-glucopyranosylurea are thereby obtained as pale yellow caramel.

Workup

  1. stirringThe mixture is further stirred at the same temperature for one hour
  2. additionare added to the reaction mixture
  3. temperaturecooling
  4. customare removed by filtration
  5. washThe filtrate is washed with an aqueous sodium bicarbonate solution
  6. customdried
  7. customevaporated
  8. customto remove solvent
  9. customThe residue thus obtained
  10. customis purified by silica gel chromatography(Solvent

Sources & evidence

ORD record
ord-3b73d51ce69b4c7b8ccc7cbf7cee77f1
Source dataset
uspto-grants-1980_01
Patent number
US04182757

Reaction notes

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