Trifluoroacetic acid → 3-methyl-4-[N'-(2-trifluoromethylphenyl)ureido]phenylacetic acid

HRID 354359Notes

Reaction equation

HRID 354359 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:22][C:23]([O:25]C(C)(C)C)=[O:24])[CH:5]=[CH:6][C:7]=1[NH:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:21])([F:20])[F:19])=[O:10].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:22][C:23]([OH:25])=[O:24])[CH:5]=[CH:6][C:7]=1[NH:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:20])([F:21])[F:19])=[O:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23512225tert-butyl 3-methyl-4-[N'-(2-trifluoromethylphenyl)ureido]phenylacetate

Product 1

HCID 235121993-methyl-4-[N'-(2-trifluoromethylphenyl)ureido]phenylacetic acidYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 3-methyl-4-[N′-(2-trifluoromethylphenyl)ureido]phenylacetate (1.06 g, 2.60 mmol) in CH2Cl2 (10 ml) was added TFA (10 ml) and the reaction mixture was stirred at room temperature for 4 hr. The reaction mixture was concentrated to a small volume and poured into ice-H2O. The resulting precipitate was collected under a reduced pressure and the crude solid was recrystallized from MeOH—CHCl3—IPE to give 3-methyl-4-[N′-(2-trifluoromethylphenyl)ureido]phenylacetic acid (702 mg, 77%) as a white crystalline powder. mp 262-263° C.; 1H-NMR (DMSO-d6) δ2.24 (s, 3 H), 3.48 (s, 2 H), 7.03 (d, J=8.3 Hz, 1 H), 7.08 (s, 1 H), 7.26-7.30 (m, 1 H), 7.61-7.69 (m, 3 H), 7.88 (d, J=8.3 Hz, 1 H), 8.39 (s, 1 H), 8.55 (s, 1 H), 12.28 (br s, 1 H); Anal. Calcd. for C17H15F3N2O3: C, 57.96; H, 4.29; N, 7.95; F, 16.18. Found: C, 57.73; H, 4.23; N, 7.92; F, 16.05.

Workup

  1. concentrationThe reaction mixture was concentrated to a small volume
  2. additionpoured into ice-H2O
  3. customThe resulting precipitate was collected under a reduced pressure
  4. customthe crude solid was recrystallized from MeOH—CHCl3—IPE

Sources & evidence

ORD record
ord-e80fc88cc5924ad1a0299469e8fa5c8c
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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