Phenyl isocyanate → [2-(3-Phenylureido)-4-methoxy-6-tert-butylphenoxy]methoxymethane

HRID 1457569Notes

Reaction equation

HRID 1457569 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:3]=1[O:4][CH2:5][O:6][CH3:7].[C:18]1([N:24]=[C:25]=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCCC1>[C:18]1([NH:24][C:25](=[O:26])[NH:1][C:2]2[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:3]=2[O:4][CH2:5][O:6][CH3:7])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 18765846(2-Amino-4-methoxy-6-tert-butylphenoxy)methoxymethane

Product 1

HCID 22099424[2-(3-Phenylureido)-4-methoxy-6-tert-butylphenoxy]methoxymethaneYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A tetrahydrofuran (THF) (20 ml) containing 2.4 g of (2-amino-4-methoxy-6-tert-butylphenoxy)methoxymethane and 1.09 ml of phenyl isocyanate was stirred at room temperature for 3 hours, and then the solvent was removed under reduced pressure. The obtained residue was crystallized from hexane, and recrystallized from an ethyl acetate-hexane mixed solution to give 2.3 g of [2-(3-phenylureido)-4-methoxy-6-tert-butylphenoxy]methoxymethane (yield: 64%, melting point: 121°-123° C., IR: 3300, 1650 cm31 1).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe obtained residue was crystallized from hexane
  3. customrecrystallized from an ethyl acetate-hexane mixed solution

Sources & evidence

ORD record
ord-8fb493ca76e141acaafdcd7cb1679df2
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Reaction notes

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