Pyridine → HCID 86744408, compound

HRID 1111027Notes

Reaction equation

HRID 1111027 reaction equation
[N:1]([CH:4]([CH2:9][C:10]([CH3:12])=[CH2:11])[C:5]([O:7][CH3:8])=[O:6])=[C:2]=[O:3].[N:13]1C=CC=CC=1.Cl.NO.C(OC)(OC)OC>C1COCC1.CO>[CH3:8][O:7][C:5]([CH:4]([NH:1][C:2]([NH2:13])=[O:3])[CH2:9][C:10]([CH3:12])=[CH2:11])=[O:6]

Participants

7

Reactant 4

HCID 1049PyridineHCID 9005Trimethyl orthoformateHCID 443297Hydroxyamine hydrochlorideHCID 22154855HCID 22154855, compound

Product 1

HCID 86744408HCID 86744408, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

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 methyl 2-isocyanato-4-methyl-4-pentenoate 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'-[1-(1-methoxycarbonyl-3-methyl-3-butenyl]urea, 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-d8b842500e1d4cabb33504c4eb71395c
Source dataset
uspto-grants-1990_12
Patent number
US04977272

Reaction notes

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