2-(Trifluoromethyl)phenyl isocyanate → ethyl 4-[N'-(2-trifluoromethylphenyl)ureido]phenylacetate

HRID 350417Notes

Reaction equation

HRID 350417 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.[F:14][C:15]([F:26])([F:25])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N:22]=[C:23]=[O:24]>C1COCC1>[F:14][C:15]([F:25])([F:26])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22][C:23](=[O:24])[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

4

Reactant 2

HCID 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 Et3 N (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) δ 1.25–1.29 (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-ec8b9e05030a4bbbb73544896756ec87
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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