Trifluoroacetic acid → 4-[N'-(2,6-dichlorophenyl)ureido]-3-methylphenylacetic acid

HRID 350435Notes

Reaction equation

HRID 350435 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10](=[O:27])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])=[CH:14][C:13]=1[CH3:26].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10](=[O:27])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:21])=[O:20])=[CH:14][C:13]=1[CH3:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23512351tert-butyl 4-[N'-(2,6-dichlorophenyl)ureido]-3-methylphenylacetate

Product 1

HCID 235122024-[N'-(2,6-dichlorophenyl)ureido]-3-methylphenylacetic acidYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 4-[N′-(2,6-dichlorophenyl)ureido]-3-methylphenylacetate (2.58 g, 6.30 mmol) in CH2Cl2 (50 ml) was added TFA (20 ml) at room temperature. After 2 h stirring, the mixture was concentrated in vacuo. The residue was triturated by the addition of water, to give 4-[N′-(2,6-dichlorophenyl)ureido]-3-methylphenylacetic acid (2.12 g, 95%) as a colorless powder. mp 274–283° C. (dec.); 1H-NMR (DMSO-d6) δ 2.24 (s, 3H), 3.46 (s, 2H), 7.00 (d, J=8.6 Hz, 1H), 7.06 (s, 1H), 7.30 (t, J=7.8 Hz, 1H), 7.52 (d, J=8.3 Hz, 2H1), 7.65 (d, J=8.2 Hz, 1H), 8.12 (s, 1H), 8.50 (s, 1H), 12.22 (br, 1H); MS (ESI) m/z 353 (M++1), 355 (M++3), 357 (M++5).

Workup

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

Sources & evidence

ORD record
ord-280c920afbfd45a0996fa07e95c98e60
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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