Hexane → HCID 53966905, compound

HRID 1733213Notes

Reaction equation

HRID 1733213 reaction equation
[Cl:1][CH2:2][CH2:3][NH:4][C:5]([N:7]([CH2:19][CH2:20][O:21][CH3:22])[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)C.[Na+].[N+:28]([O-])([N+]([O-])=O)=[O:29].CCCCCC>O1CCCC1.C(O)(=O)C.CO>[Cl:1][CH2:2][CH2:3][N:4]([N:28]=[O:29])[C:5]([N:7]([CH2:19][CH2:20][O:21][CH3:22])[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 8058Hexane2×HCID 25352Nitrogen oxide (N2O4)HCID 517045Sodium AcetateHCID 53787329HCID 53787329, compound

Product 1

HCID 53966905HCID 53966905, compoundYield 46.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3.4 g of 1-(2-chloroethyl)-3-(2-methoxyethyl)-3-(D-mannopyranosyl)urea are dissolved in a mixture of 40 ml of tetrahydrofuran and 10 ml of acetic acid, and 17 g of sodium acetate anhydrate are added thereto. 6 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. 70 ml of hexane are added to the reaction mixture, and said mixture is filtered. The filtrate is condensed under reduced pressure. A mixture of 200 ml of hexane and 4 ml of methanol is added to the residue. After the resultant oil is washed with ether, said oil is dissolved in 50 ml of ethyl acetate. 10 ml of water are added to the ethyl acetate solution, and the mixture is shaken. Then, the ethyl acetate layer is collected therefrom, dried and evaporated under reduced pressure. 1.7 g of 1-(2-chloroethyl)-1-nitroso-3-(2-methoxyethyl)-3-(D-mannopyranosyl)urea is thereby obtained as pale yellow caramel.

Workup

  1. additionare added
  2. temperaturecooling
  3. stirringThe mixture is further stirred at the same temperature for 10 minutes
  4. filtrationis filtered
  5. customcondensed under reduced pressure
  6. additionis added to the residue
  7. washAfter the resultant oil is washed with ether
  8. dissolutionis dissolved in 50 ml of ethyl acetate
  9. addition10 ml of water are added to the ethyl acetate solution
  10. stirringthe mixture is shaken
  11. customThen, the ethyl acetate layer is collected
  12. customdried
  13. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f7c849431f27475aa537eb86756e13e7
Source dataset
uspto-grants-1980_12
Patent number
US04241053

Reaction notes

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