Methanol → HCID 13092708, compound

HRID 2051791Notes

Reaction equation

HRID 2051791 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].C(=O)([O-])[O-].[Na+].[Na+].[N+:26]([O-])([N+]([O-])=O)=[O:27].CO>O1CCCC1.C(Cl)Cl.O>[Cl:1][CH2:2][CH2:3][N:4]([N:26]=[O:27])[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

8

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 25352Nitrogen oxide (N2O4)HCID 54470639HCID 54470639, compound

Product 1

HCID 13092708HCID 13092708, compoundYield 72.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

3.0 g of 1-(2-chloroethyl)-3-methyl-3-D-glucopyranosylurea prepared in the same manner as described in Example 1-(1) are dissolved in a mixture of 80 ml of tetrahydrofuran and 80 ml of methylene chloride, and 15 g of sodium carbonate anhydrate are added thereto. 5 g of nitrogen tetroxide gas are introduced into the mixture for 10 minutes under ice-cooling. The mixture is further stirred at the same temperature for 10 minutes. After the reaction, 10 ml of methanol and 3 ml of water are added to the mixture, and the mixture is stirred for 10 minutes. Said mixture is dried, filtered and evaporated to remove solvent. Then, the residue obtained is purified by silica gel chromatography (Solvent: ethyl acetate-chloroform-methanol(5:2:1)). 2.4 g of 1-(2-chloroethyl)-1-nitroso-3-methyl-3-D-glucopyranosylurea are thereby obtained as a pale yellow powder.

Workup

  1. additionare added
  2. temperaturecooling
  3. additionare added to the mixture
  4. stirringthe mixture is stirred for 10 minutes
  5. customis dried
  6. filtrationfiltered
  7. customevaporated
  8. customto remove solvent
  9. customThen, the residue obtained
  10. customis purified by silica gel chromatography (Solvent: ethyl acetate-chloroform-methanol(5:2:1))

Sources & evidence

ORD record
ord-e67058fd443f4b67acff1dcc848274df
Source dataset
uspto-grants-1980_01
Patent number
US04182757

Reaction notes

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