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

HRID 551722Notes

Reaction equation

HRID 551722 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.BrN1C(=O)CCC1=O>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 67184N-bromobutanimideHCID 249880741,2-Bis(2-methoxyethyl) 1,2-hydrazinedicarboxylate

Product 1

HCID 533844152-methoxyethyl N-(2-methoxyethoxycarbonylimino)carbamateYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1,2-hydrazinedicarboxylic acid bis(2-methoxyethyl) ester (45 g, 191 mmol), pyridine (15.09 g, 191 mmol), and toluene (450 ml) were added to a 1000 ml flask, and N-bromosuccinimide (37.31 g, 210 mmol) was slowly added thereto at 20° C., followed by allowing the reaction to proceed for two hours. After the reaction, the solution was washed with water (180 mL, ×2), and dehumidified with anhydrous magnesium sulfate, followed by concentration to dryness. The resulting solid was recrystallized with toluene (67.5 ml) and hexane (337.5 ml), to give azodicarboxylic acid bis(2-methoxyethyl) ester as a pale yellow crystal (39.26 g, yield: 88.0%).

Workup

  1. customat 20° C.
  2. customthe reaction
  3. customAfter the reaction
  4. washthe solution was washed with water (180 mL, ×2)
  5. concentrationfollowed by concentration to dryness
  6. customThe resulting solid was recrystallized with toluene (67.5 ml) and hexane (337.5 ml)

Sources & evidence

ORD record
ord-56f6008f2f194b54a0590036eb62ce9d
Source dataset
uspto-grants-2011_05
Patent number
US07947816B2

Reaction notes

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