Phenyl isocyanate → ethyl 4-(N'-phenylureido)phenylacetate

HRID 354348Notes

Reaction equation

HRID 354348 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.CCN(CC)CC.[C:21]1([N:27]=[C:28]=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1>[C:21]1([NH:27][C:28](=[O:29])[NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 225219p-Aminophenylacetic acid ethyl ester

Product 1

HCID 23512302ethyl 4-(N'-phenylureido)phenylacetateYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 4-aminophenylacetate (6.43 g, 35.9 mmol) and Et3N (5.50 ml, 39.5 mmol) in THF (70 ml) was added phenyl isocyanate (3.90 ml, 35.9 mmol), and the reaction mixture was stirred at room temperature for 4 days. Resulting precipitate was collected under a reduced pressure and the filtrate was washed with n-hexane to give ethyl 4-(N′-phenylureido)phenylacetate (9.64 g, 90%) as a white crystalline powder. mp 153-155° C.; 1H-NMR (CDCl3) δ1.26 (t, J=7.1 Hz, 3 H), 3.52 (s, 2 H), 4.15 (q, J=7.1 Hz, 2 H), 6.98-7.04 (m, 1 H), 7.07-7.11 (m, 4 H), 7.18-7.25 (m, 5 H), 7.42 (s, 1 H); MS (FAB) m/z 299 (M++1); Anal. Calcd. for C17H18N2O3: C, 68.44; H, 6.08; N, 9.39. Found: C, 68.22; H, 6.10; N, 9.36.

Workup

  1. customResulting precipitate
  2. customwas collected under a reduced pressure
  3. washthe filtrate was washed with n-hexane

Sources & evidence

ORD record
ord-1db723ec9ac64c21858cc07c80b8ffeb
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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