Trifluoroacetic acid → 3-methyl4-(N'-phenylureido)phenylacetic acid

HRID 354351Notes

Reaction equation

HRID 354351 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])[CH:5]=[CH:6][C:7]=1[NH:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:10].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:18][C:19]([OH:21])=[O:20])[CH:5]=[CH:6][C:7]=1[NH:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23512058tert-butyl 3-methyl4-(N'-phenylureido)phenylacetate

Product 1

HCID 235117053-methyl4-(N'-phenylureido)phenylacetic acidYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 3-methyl-4-(N′-phenylureido)phenylacetate (1.12 g, 3.29 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 to give 3-methyl-4(N′-phenylureido)phenylacetic acid (680 mg, 73%) as white needles. 1H-NMR (DMSO-d6) δ2.22 (s, 3 H), 3.46 (s, 2 H), 6.93-7.05 (m, 3 H), 7.25-7.29 (m, 2 H), 7.43-7.46 (m, 2 H), 7.72-7.74 (m, 1 H), 7.90 (s, 1 H), 8.98 (s, 1 H), 12.26 (br s, 1 H); Anal. Calcd. for C16H16N2O3: C, 67.59; H, 5.67; N, 9.85. Found: C, 67.47; H, 5.68; N, 9.73.

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

Sources & evidence

ORD record
ord-5405b4afc9894dcf812149513c8a2928
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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