4-Phenoxyphenyl isocyanate → 1-Hydroxy-1-(1-ethylpropyl)-3-(4-phenoxyphenyl)urea

HRID 976641Notes

Reaction equation

HRID 976641 reaction equation
[CH2:1]([CH:3]([NH:6][OH:7])[CH2:4][CH3:5])[CH3:2].[O:8]([C:15]1[CH:20]=[CH:19][C:18]([N:21]=[C:22]=[O:23])=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O1CCCC1>[OH:7][N:6]([CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[C:22]([NH:21][C:18]1[CH:19]=[CH:20][C:15]([O:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:16][CH:17]=1)=[O:23]

Participants

4

Reactant 2

HCID 27348964-Phenoxyphenyl isocyanateHCID 19073513N-(pentan-3-yl)hydroxylamine2×

Product 1

HCID 199673811-Hydroxy-1-(1-ethylpropyl)-3-(4-phenoxyphenyl)ureaYield 50.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-(1-ethylpropyl)hydroxylamine (1.13 g, 11 mmole, Compound 39, Part B) in tetrahydrofuran (30 mL) was charged with 4-phenoxyphenylisocyanate (2.1 g, 10 mmole) and maintained at ambient temperature overnight. The solvent was removed in vacuo to yield 3.2 g of the crude product as a white solid. Recrystallization from hexanesethyl acetate provided 1.6 g of the desired product as a white crystalline solid, m.p. 124°-125° C. Analysis: Calculated for: C18H22N2O3 : %C, 68.77; %H, 7.05; %N, 8.91; Found: %C, 68.44; %H, 7.09; %N, 8.82.

Workup

  1. customThe solvent was removed in vacuo
  2. customto yield 3.2 g of the crude product as a white solid
  3. customRecrystallization from hexanesethyl acetate

Sources & evidence

ORD record
ord-0172f93dfd3b4ccfb0abf7fa379994cc
Source dataset
uspto-grants-1997_03
Patent number
US05612377

Reaction notes

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