Trifluoroacetic acid → 4-[N'-(2-chlorophenyl)ureido]-3-methylphenylacetic acid

HRID 350423

Reaction equation

HRID 350423 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:26])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20]C(C)(C)C)=[O:19])=[CH:13][C:12]=1[CH3:25].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:26])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([OH:20])=[O:19])=[CH:13][C:12]=1[CH3:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23512001tert-butyl 4-[N'-(2-chlorophenyl)ureido]-3-methylphenylacetate

Product 1

HCID 235120494-[N'-(2-chlorophenyl)ureido]-3-methylphenylacetic acidYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 4-[N′-(2-chlorophenyl)ureido]-3-methylphenylacetate (1.57 g, 4.19 mmol) in CH2Cl2 (10 ml) was added TFA (6 ml) at room temperature. After 4 h stirring, the mixture was concentrated in vacuo. The residue was triturated by the addition of water to give 4-[N′-(2-chlorophenyl)ureido]-3-methylphenylacetic acid (1.33 g, 100%) as a yellow powder. mp 243–245° C. (dec.); 1H-NMR (CDCl3) δ 2.24 (s, 3H), 3.47 (s, 2H), 6.99–7.08 (m, 3H), 7.28 (t, J=7.6 Hz, 1H), 7.44 (dt, J=8.0, 2.4 Hz, 1H), 7.66 (dd, J=8.3, 1.9 Hz, 1H), 8.13 (dd, J=6.1, 1.7 Hz, 1H), 8.61 (d, J=6.3 Hz, 2H); MS (ESI), m/z 319 (M++1), 321 (M++3); Anal. Calcd for C16H15ClN2O3.0.7TFA: C, 59.33; H, 4.65; Cl, 10.85; N, 8.57. Found: C, 59.23; H, 4.64; Cl, 10.90; N, 8.40.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe residue was triturated by the addition of water

Sources & evidence

ORD record
ord-52ec01c497c44bc1b873e9b0aedd742f
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Linked notes

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