Pyridine → 2-methoxyethyl N-(2-methoxyethoxycarbonylimino)carbamate

HRID 1162862Notes

Reaction equation

HRID 1162862 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]([NH:8][NH:9][C:10]([O:12][CH2:13][CH2:14][O:15][CH3:16])=[O:11])=[O:7].N1C=CC=CC=1.ClCl>C1(C)C=CC=CC=1>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]([N:8]=[N:9][C:10]([O:12][CH2:13][CH2:14][O:15][CH3:16])=[O:11])=[O:7]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24526ChlorineHCID 249880741,2-Bis(2-methoxyethyl) 1,2-hydrazinedicarboxylate

Product 1

HCID 533844152-methoxyethyl N-(2-methoxyethoxycarbonylimino)carbamateYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution obtained by adding 1,2-hydrazinedicarboxylic acid bis(2-methoxyethyl) ester (1 g, 4.23 mmol), pyridine (0.34 g, 4.23 mmol), and toluene (10 ml) to a 30 ml flask, followed by cooling with an ice bath, chlorine gas was blown for 30 minutes. After the reaction, the solution was washed with water (1 mL,×2), and dehumidified with anhydrous magnesium sulfate, followed by concentration to dryness. The solid was recrystallized with toluene (1.5 mL) and hexane (7.5 mL), to give azodicarboxylic acid bis(2-methoxyethyl) ester as a pale yellow crystal (0.59 g, yield: 60%).

Workup

  1. customTo a solution obtained
  2. temperatureby cooling with an ice bath
  3. customAfter the reaction
  4. washthe solution was washed with water (1 mL,×2)
  5. concentrationfollowed by concentration to dryness
  6. customThe solid was recrystallized with toluene (1.5 mL) and hexane (7.5 mL)

Sources & evidence

ORD record
ord-150ad08fee174e299efed3dbe3226afa
Source dataset
uspto-grants-2010_10
Patent number
US07820802B2

Reaction notes

Loading…