Hydrochloric Acid → {4-[(Anilinocarbonyl)amino]phenyl}acetic acid

HRID 350412

Reaktionsgleichung

Reaktionsgleichung von HRID 350412
[C:1]1([NH:7][C:8](=[O:22])[NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([O:19]CC)=[O:18])=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=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>[C:1]1([NH:7][C:8](=[O:22])[NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:19])=[O:18])=[CH:12][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23512302ethyl 4-(N'-phenylureido)phenylacetate

Produkt 1

HCID 564698{4-[(Anilinocarbonyl)amino]phenyl}acetic acidAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 56841950ICE protocol 1KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of ethyl 4-(N′-phenylureido)phenylacetate (9.64 g, 32.3 mmol) in THF (80 ml) was added 0.5 N NaOH (80 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 to give 4-(N′-phenylureido)phenylacetic acid (8.14 g, 93%) as a white crystalline powder. MS (FAB) m/z 271 (M++1); Anal. Calcd for C15H14N2O3: C, 66.66; H, 5.22; N, 10.36. Found: C, 66.45; H, 5.22; N, 10.30.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7b01fdbf9f264ab8a80c402d3c9f1890
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179819B2

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