Pyridine → HCID 86741869, compound

HRID 649663Notes

Reaction equation

HRID 649663 reaction equation
[N-:1]=[C:2]=[O:3].[CH3:4][O:5][C:6](=[O:10])[CH:7]([CH3:9])[NH2:8].[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl.N[OH:19].C(OC)(OC)OC.[CH2:27]1COC[CH2:28]1>CO>[OH:19][N:11]=[CH:16][C:15]1[CH:28]=[CH:27][C:12]([NH:1][C:2]([NH:8][CH:7]([C:6]([O:5][CH3:4])=[O:10])[CH3:9])=[O:3])=[CH:13][CH:14]=1

Participants

7

Reactant 5

HCID 1049PyridineHCID 8028Tetrahydrofuran2×HCID 9005Trimethyl orthoformateHCID 443297Hydroxyamine hydrochlorideHCID 86741870HCID 86741870, compound

Product 1

HCID 86741869HCID 86741869, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-[4-(hydroxyiminomethyl)phenyl]-N'-(1-methoxycarbonylethyl)urea is prepared as follows: A solution of 0.1 mol of 4-aminobenzaldehyde ethylene glycol acetal in 100 mL of anhydrous THF is added dropwise over 10 minutes to a solution of 0.1 mol DL-alanine methyl ester isocyanate and 0.35 mol pyridine in 100 mL THF at room temperature under N2. The yellow reaction mixture is stirred at room temperature for 2 hours. After 1/2 hour a yellow-orange precipitate begins to form. After 2 hours the solvent is removed by rotary evaporator to give an orange, semisolid mass. A solution of 0.11 mol hydroxylamine hydrochloride and 0.1 mol trimethyl orthoformate in CH3OH is added, and the reaction mixture is heated to reflux under N2 for 1 hour. The reaction mixture is reduced to about 1/4 volume by rotary evaporator, and water is added. Off-white crystals of product form after 2 hours of stirring. The crystals are isolated by filtration and dried overnight in a vacuum oven at 50°-55° C. The yield of product (mp 143°-145.5° C.) is about 60%.

Workup

  1. waitAfter 1/2 hour a yellow-orange precipitate begins
  2. customto form
  3. customAfter 2 hours the solvent is removed by rotary evaporator
  4. customto give an orange, semisolid mass
  5. temperaturethe reaction mixture is heated
  6. temperatureto reflux under N2 for 1 hour
  7. customThe reaction mixture is reduced to about 1/4 volume by rotary evaporator, and water
  8. additionis added
  9. stirringOff-white crystals of product form after 2 hours of stirring
  10. customThe crystals are isolated by filtration
  11. customdried overnight in a vacuum oven at 50°-55° C

Sources & evidence

ORD record
ord-917e30db52f34acc90cfde4ba1a59f50
Source dataset
uspto-grants-1988_04
Patent number
US04740611

Reaction notes

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