Hydrochloric Acid → [4-({[2-(Trifluoromethyl)phenyl]carbamoyl}amino)phenyl]acetic acid

HRID 354355

Reaction equation

HRID 354355 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=[O:24])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([O:21]CC)=[O:20])=[CH:14][CH:13]=1.[OH-].[Na+].Cl>C1COCC1.C[C@H]1O[C@H]2[C@H](O)[C@@H](O)[C@H](OC3C4C(=CC5OCOC=5C=4)[C@@H](C4C=C(OC)C(O)=C(OC)C=4)[C@@H]4[C@@H]3COC4=O)O[C@@H]2CO1.C1COP(NCCCl)(=O)N(CCCl)C1.[NH2-].[NH2-].Cl[Pt+2]Cl>[F:1][C:2]([F:25])([F:26])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=[O:24])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:21])=[O:20])=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23511916ethyl 4-[N'-(2-trifluoromethylphenyl)ureido]phenylacetate

Product 1

HCID 17255620[4-({[2-(Trifluoromethyl)phenyl]carbamoyl}amino)phenyl]acetic acidYield 51%

Reagents, catalysts & solvents 2

HCID 56841950ICE protocol 1CatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 4-[N′-(2-trifluoromethylphenyl)ureido]phenylacetate (1.93 g, 5.27 mmol) in THF (10 ml) was added 1 N NaOH (10 ml) and the reaction mixture was heated under reflux for 5 hr. After cooled to room temperature, the mixture was poured into ice-1 N HCl. The resulting precipitate was collected under a reduced pressure and the crude solid was recrystallized from MeOH—CHCl3—IPE to give 4-[N′-(2-trifluoromethylphenyl)ureido]phenylacetic acid (910 mg, 51%) as a white crystalline powder. mp 224-225° C.; 1H-NMR (DMSO-d6) δ3.50 (s, 2 H), 7.18 (d, J=8.3 Hz, 2 H), 7.25-7.29 (m, 1 H), 7.40 (d, J=8.3 Hz, 2H), 7.62-7.69 (m, 2 H), 7.95-7.97 (m, 1 H), 8.06 (s, 1 H), 9.37 (s, 1 H), 12.27 (br s, 1H); Anal. Calcd. for C16H13F3N2O3: C, 56.81; H, 3.87; N, 8.28; F, 16.85. Found: C, 56.68; H, 3.87; N, 8.16; F, 16.89.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 5 hr
  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-6ba0968d7635407aae6f314deb3ed1bb
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Linked notes

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