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

HRID 350420Notes

Reaction equation

HRID 350420 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].[F:17][C:18]([F:29])([F:28])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N:25]=[C:26]=[O:27]>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:26]([NH:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:18]([F:17])([F:28])[F:29])=[O:27]

Participants

4

Reactant 2

HCID 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 Et3 N (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) δ 1.44 (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-74f1bbea67424ee68008421524b83584
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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