Ethanol → HCID 86737399, compound

HRID 1733216Notes

Reaction equation

HRID 1733216 reaction equation
[Cl:1][CH2:2][CH2:3][NH:4][C:5]([N:7]([CH2:17][CH2:18][CH2:19][O:20][CH3:21])[CH:8]1[O:16][CH2:15][C@H:13]([OH:14])[C@H:11]([OH:12])[C@H:9]1[OH:10])=[O:6].[N:22]([O-])=[O:23].[Na+].C(O)C.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]([CH2:17][CH2:18][CH2:19][O:20][CH3:21])[CH:8]1[O:16][CH2:15][C@H:13]([OH:14])[C@H:11]([OH:12])[C@H:9]1[OH:10])=[O:6]

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 23668193Sodium NitriteHCID 54230428HCID 54230428, compound

Product 1

HCID 86737399HCID 86737399, compoundYield 33.4%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

3.3 g of 1-(2-chloroethyl)-3-(3-methoxy-n-propyl)-3-(L-arabinopyranosyl)urea are dissolved in 15 ml of formic acid, and 1.5 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 one hour. After the reaction, 15 ml of ethanol 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: ethyl acetate-chloroform-methanol=5:2:1). 1.2 g of 1-(2-chloroethyl)-1-nitroso-3-(3-methoxy-n-propyl)-3-(L-arabinopyranosyl)urea are thereby obtained as 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: ethyl acetate-chloroform-methanol=5:2:1)

Sources & evidence

ORD record
ord-28627726216f4c0bbc1df0dfd7ac1ccf
Source dataset
uspto-grants-1980_12
Patent number
US04241053

Reaction notes

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