HCID 20378115, compound → HCID 20378104, compound

HRID 2051853Notes

Reaction equation

HRID 2051853 reaction equation
[Cl:1][CH2:2][CH2:3][NH:4][C:5]([N:7]([CH3:11])[CH2:8][CH2:9][OH:10])=[O:6].[N:12]([O-])=[O:13].[Na+]>C(O)(=O)C>[Cl:1][CH2:2][CH2:3][N:4]([N:12]=[O:13])[C:5]([N:7]([CH3:11])[CH2:8][CH2:9][OH:10])=[O:6]

Participants

4

Reactant 2

HCID 20378115HCID 20378115, compoundHCID 23668193Sodium Nitrite2×

Product 1

HCID 20378104HCID 20378104, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.9 g of 1-(2-chloroethyl)-3-methyl-3-(2-hydroxyethyl)urea is dissolved in 10 ml of acetic acid, and 0.9 g of sodium nitrite is added thereto under stirring. The mixture is stirred at room temperature for one hour. Then, 0.5 g of sodium nitrite is again added to the mixture, and said mixture is further stirred at the same temperature for 4 hours. After the reaction, the mixture is freeze-dried, and the residue obtained is purified by silica gel chromatography (Solvent: chloroform-methanol=10:1). 0.7 g of 1-(2-chloroethyl)-1-nitroso-3-methyl-3-(2-hydroxyethyl)urea is thereby obtained as a pale yellow oil.

Workup

  1. stirringThe mixture is stirred at room temperature for one hour
  2. stirringis further stirred at the same temperature for 4 hours
  3. customAfter the reaction
  4. customthe mixture is freeze-dried
  5. customthe residue obtained
  6. customis purified by silica gel chromatography (Solvent: chloroform-methanol=10:1)

Sources & evidence

ORD record
ord-ff6278c8f2584f3997a3ba84c91ecbd5
Source dataset
uspto-grants-1980_01
Patent number
US04182757

Reaction notes

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