Triethylamine → tert-butyl 3-methyl-4-[N'-(2-trifluoromethylphenyl)ureido]phenylacetate

HRID 354358Notes

Reaction equation

HRID 354358 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:4][C:3]=1[CH3:16].CCN(CC)CC.[F:24][C:25]([F:36])([F:35])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N:32]=[C:33]=[O:34]>C1COCC1>[CH3:16][C:3]1[CH:4]=[C:5]([CH2:8][C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH:6]=[CH:7][C:2]=1[NH:1][C:33]([NH:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[C:25]([F:24])([F:35])[F:36])=[O:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 167942-(Trifluoromethyl)phenyl isocyanateHCID 23512173Tert-butyl 4-amino-3-methylphenylacetate

Product 1

HCID 23512225tert-butyl 3-methyl-4-[N'-(2-trifluoromethylphenyl)ureido]phenylacetateYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl 4-amino-3-methylphenylacetate (927 mg, 4.19 mmol) and Et3N (645 μl, 4.63 mmol) in THF (10 ml) was added 2-trifluoromethylphenyl isocyanate (633 μl, 4.19 mmol) and the reaction mixture was stirred at room temperature for 2 days. The reaction mixture was concentrated to a small volume and diluted with n-hexane. Resulting precipitate was collected under a reduced pressure and the filtrate was washed with n-hexane to give tert-butyl 3-methyl-4-[N′-(2-trifluoromethylphenyl)ureido]phenylacetate (1.06 g, 62%) as a white crystalline powder. mp 178-180° C.; 1H-NMR (CDCl3) δ1.44 (s, 9 H), 2.25 (s, 3 H), 3.51 (s, 2 H), 6.38 (br s, 1 H), 7.12-7.18 (m, 3 H), 7.36-7.37 (m, 1 H), 7.49-7.53 (m, 2 H), 8.13-8.16 (m, 1 H).

Workup

  1. concentrationThe reaction mixture was concentrated to a small volume
  2. additiondiluted with n-hexane
  3. customResulting precipitate
  4. customwas collected under a reduced pressure
  5. washthe filtrate was washed with n-hexane

Sources & evidence

ORD record
ord-56ca7e2d56374e7d924e25712b3efac4
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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