Pyridine → 4-(hydroxyiminomethyl)phenyl-N'-ethoxycarbonylmethylurea

HRID 1111004Notes

Reaction equation

HRID 1111004 reaction equation
[N-:1]=[C:2]=[O:3].[CH2:4]([O:6][C:7](=[O:10])[CH2:8][NH2:9])[CH3:5].[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:9][CH2:8][C:7]([O:6][CH2:4][CH3:5])=[O:10])=[O:3])=[CH:13][CH:14]=1

Participants

7

Reactant 5

HCID 1049PyridineHCID 8028Tetrahydrofuran2×HCID 9005Trimethyl orthoformateHCID 443297Hydroxyamine hydrochlorideHCID 86647037Ethyl 2-aminoacetate isocyanate

Product 1

HCID 867443964-(hydroxyiminomethyl)phenyl-N'-ethoxycarbonylmethylurea

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 ethyl 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'-ethoxycarbonylmethylurea, 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-1f1f03d57a924e63abea84909cf176b6
Source dataset
uspto-grants-1990_12
Patent number
US04977272

Reaction notes

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