Pyridine → N-[4-(hydroxyiminomethyl)phenyl]-N'-isopropoxycarbonylmethylurea

HRID 1111010Notes

Reaction equation

HRID 1111010 reaction equation
[N-:1]=[C:2]=[O:3].[CH:4]([O:7][C:8](=[O:11])[CH2:9][NH2:10])([CH3:6])[CH3:5].[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl.N[OH:20].C(OC)(OC)OC.[CH2:28]1COC[CH2:29]1>CO>[OH:20][N:12]=[CH:17][C:16]1[CH:29]=[CH:28][C:13]([NH:1][C:2]([NH:10][CH2:9][C:8]([O:7][CH:4]([CH3:6])[CH3:5])=[O:11])=[O:3])=[CH:14][CH:15]=1

Participants

7

Reactant 5

HCID 1049PyridineHCID 8028Tetrahydrofuran2×HCID 9005Trimethyl orthoformateHCID 443297Hydroxyamine hydrochlorideHCID 86742133Glycine isopropyl ester isocyanate

Product 1

HCID 86744399N-[4-(hydroxyiminomethyl)phenyl]-N'-isopropoxycarbonylmethylurea

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.1 mol of p-aminobenzaldehyde ethylene glycol acetal in 100 mL of anhydrous THF is added dropwise over 10 minutes to a solution of 0.1 mol of glycine isopropyl 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 0.11 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-[4-(hydroxyiminomethyl)phenyl]-N'-isopropoxycarbonylmethylurea, is isolated by filtration and dried in vacuo.

Workup

  1. additionis added
  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-e90d306c58bd46aabea8e52f051f4a49
Source dataset
uspto-grants-1990_12
Patent number
US04977272

Reaction notes

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