Dichloromethane → HCID 54311612, compound

HRID 1733248Notes

Reaction equation

HRID 1733248 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([N:20]=[O:21])[C:5]([N:7]([CH2:17][CH:18]=[CH2:19])[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].ClC1C=CC=C(C(OO)=[O:30])C=1.C(Cl)Cl>C1C=CC=CC=1>[Cl:1][CH2:2][CH2:3][N:4]([N:20]=[O:21])[C:5]([N:7]([CH2:17][CH:18]1[CH2:19][O:30]1)[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

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 54133889HCID 54133889, compound

Product 1

HCID 54311612HCID 54311612, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 5.3 g of 1-(2-chloroethyl)-1-nitroso-3-(2-propenyl)-3-(L-arabinopyranosyl)urea, 5.9 g of meta-chloroperbenzoic acid, 50 ml of methylene chloride and 50 ml of benzene is stirred at room temperature for 3 hours. After the reaction, the mixture is condensed under reduced pressure. The residue obtained is washed with ether and then purified by silica gel chromatography (Solvent: ethyl acetate). 0.9 g of 1-(2-chloroethyl)-1-nitroso-3-(oxiran-2-yl-methyl)-3-(L-arabinopyranosyl)urea is thereby obtained as yellow caramel.

Workup

  1. customAfter the reaction
  2. customcondensed under reduced pressure
  3. customThe residue obtained
  4. washis washed with ether
  5. custompurified by silica gel chromatography (Solvent: ethyl acetate)

Sources & evidence

ORD record
ord-f7063c35a6c34d248fb55917ba3ae8a8
Source dataset
uspto-grants-1980_12
Patent number
US04241052

Reaction notes

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