Pyridine → HCID 57053574, compound

HRID 1111024Notes

Reaction equation

HRID 1111024 reaction equation
[N-:1]=[C:2]=[O:3].[C:4]1([O:10][C:11](=[O:14])[CH2:12][NH2:13])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.N1C=CC=CC=1.Cl.NO.C(OC)(OC)OC>C1COCC1.CO>[O:10]([C:11]([CH2:12][NH:13][C:2](=[O:3])[NH2:1])=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 9005Trimethyl orthoformateHCID 443297Hydroxyamine hydrochlorideHCID 86742137HCID 86742137, compound

Product 1

HCID 57053574HCID 57053574, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.1 mol of 4-(allylamino)benzaldehyde ethylene glycol acetal in 100 mL of anhydrous THF is added dropwise over 10 minutes to a solution of 0.1 mol of the glycine phenyl ester isocyanate and 0.35 mol pyridine in 100 mL THF at room temperature under N2. The reaction mixture is stirred at room temperature for 2 hours. After 2 hours the solvent is removed by rotary evaporator. A solution of 0.1 mmol 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. The product, N-allyl-N-4-(hydroxyiminomethyl)phenyl]-N'-phenoxycarbonylmethylurea, is isolated by filtration and dried in vacuo.

Workup

  1. customAfter 2 hours the solvent is removed by rotary evaporator
  2. temperaturethe reaction mixture is heated
  3. temperatureto reflux under N2 for 1 hour
  4. customThe reaction mixture is reduced to about 1/4 volume by rotary evaporator, and water
  5. additionis added

Sources & evidence

ORD record
ord-3a3463137b8d4fb3afb290067d229920
Source dataset
uspto-grants-1990_12
Patent number
US04977272

Reaction notes

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