Methanol → HCID 53768910, compound

HRID 1733228Notes

Reaction equation

HRID 1733228 reaction equation
[Cl:1][CH2:2][CH2:3][NH:4][C:5]([N:7]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]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].C(=O)([O-])[O-].[Na+].[Na+].[N+:31]([O-])([N+]([O-])=O)=[O:32].CO>O1CCCC1.C(Cl)Cl.O>[Cl:1][CH2:2][CH2:3][N:4]([N:31]=[O:32])[C:5]([N:7]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]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

8

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 25352Nitrogen oxide (N2O4)HCID 22813516HCID 22813516, compound

Product 1

HCID 53768910HCID 53768910, compoundYield 70.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

3.7 g of 1-(2-chloroethyl)-3-cyclohexyl-3-(D-galactopyranosyl) urea are dissolved in a mixture of 60 ml of tetrahydrofuran and 60 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 and stirring. 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 aqueous mixture is stirred vigorously for 10 minutes. Said aqueous mixture is dried and filtered. The filtrate is evaporated to remove solvent. Then, the residue obtained is purified by silica gel chromatography (Solvent: ethyl acetate-chloroform-methanol (5:2:1)). 2.8 g of 1-(2-chloroethyl)-1-nitroso-3-cyclohexyl-3-(D-galactopyranosyl)urea are thereby obtained as yellow caramel.

Workup

  1. additionare added
  2. temperaturecooling
  3. stirringThe mixture is further stirred at the same temperature for 10 minutes
  4. additionare added to the mixture
  5. stirringthe aqueous mixture is stirred vigorously for 10 minutes
  6. customis dried
  7. filtrationfiltered
  8. customThe filtrate is evaporated
  9. customto remove solvent
  10. customThen, the residue obtained
  11. customis purified by silica gel chromatography (Solvent: ethyl acetate-chloroform-methanol (5:2:1))

Sources & evidence

ORD record
ord-675b10dd43574d9da083ff862a994ee4
Source dataset
uspto-grants-1980_12
Patent number
US04241052

Reaction notes

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