Triethylamine → ethyl 4-[N'-(2-trifluoromethylphenyl)ureido]phenylacetate

HRID 354354Notes

Reaction equation

HRID 354354 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.[F:21][C:22]([F:33])([F:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N:29]=[C:30]=[O:31]>C1COCC1>[F:21][C:22]([F:32])([F:33])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[NH:29][C:30](=[O:31])[NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 167942-(Trifluoromethyl)phenyl isocyanateHCID 225219p-Aminophenylacetic acid ethyl ester

Product 1

HCID 23511916ethyl 4-[N'-(2-trifluoromethylphenyl)ureido]phenylacetateYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 4-aminophenylacetate (1.13 g, 6.31 mmol) and Et3N (965 ml, 6.92 mmol) in THF (10 ml) was added 2-trifluoromethylphenyl isocyanate (953 ml, 6.31 mmol) and the reaction mixture was stirred at room temperature for 2 days. Resulting precipitate was collected under a reduced pressure and the filtrate was washed with n-hexane to give ethyl 4-[N′-(2-trifluoromethylphenyl)ureido]phenylacetate (1.93 g, 84%) as white needles. mp 137-139° C.; 1H-NMR (CDCl3) δ1.25-1.29 (m, 3 H), 3.59 (s, 2 H), 4.15-4.20 (m, 2 H), 7.05 (br s, 1 H), 7.13-7.23 (m, 6 H), 7.47-7.51 (m, 1 H), 7.54-7.56 (m, 1 H), 8.01-8.03 (m, 1 H).

Workup

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

Sources & evidence

ORD record
ord-d0b85104dfbc49398a541fb37c29a0ab
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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