4-[4-(4-Fluoro-phenyl)-thiazol-2-yl]-2'-nitro-biphenyl-2-carboxylic acid methyl ester → 4-[4-(4-Fluoro-phenyl)-thiazol-2-yl]-2'-nitro-biphenyl-2-carboxylic acid

HRID 1519259Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1519259
[OH-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([C:15]3[CH:16]=[C:17]([C:30]([OH:32])=[O:31])[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[N+:27]([O-:29])=[O:28])=[CH:19][CH:20]=3)[S:13][CH:14]=2)=[CH:6][CH:5]=1.COC(C1C(C2C=CC=CC=2[N+]([O-])=O)=CC=C(C2SC=C(C3C=CC(F)=CC=3)N=2)C=1)=O>O.O1CCOCC1>[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([C:15]3[CH:16]=[C:17]([C:30]([OH:32])=[O:31])[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[N+:27]([O-:29])=[O:28])=[CH:19][CH:20]=3)[S:13][CH:14]=2)=[CH:6][CH:5]=1

Komponenten

5

Edukt 2

HCID 866798374-[4-(4-Fluoro-phenyl)-thiazol-2-yl]-2'-nitro-biphenyl-2-carboxylic acid methyl esterHCID 866798394-[4-(4-Fluoro-phenyl)-thiazol-2-yl]-2'-nitro-biphenyl-2-carboxylic acid Sodium hydroxide

Produkt 1

HCID 715358134-[4-(4-Fluoro-phenyl)-thiazol-2-yl]-2'-nitro-biphenyl-2-carboxylic acidAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

4-[4-(4-Fluoro-phenyl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid Sodium hydroxide (40 mg, 1 mmol) was added to a suspension of 4-[4-(4-fluoro-phenyl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid methyl ester (40 mg) in a mixture of water (1 mL) and dioxane (1 mL). The resulting mixture was heated at 50° C. for 4 h. The solvent was evaporated and water (5 mL) was added. The mixture was filtered and the filtrate was made acidic to pH 3 by the addition of concentrated HCl. The precipitate was collected by filtration and dried to give 4-[4-(4-fluoro-phenyl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid (45 mg, 58% for two steps). 1H NMR (300 MHz, DMSO-d6) δ 13.21 (br s, 1H), 8.65 (s, 1H), 8.17-8.33 (m, 5H), 7.86 (t, J=7.6 Hz, 1H), 7.73 (t, J=7.8 Hz, 1H), 7.52 (t, J=8.5 Hz, 2H), 7.40 (t, J=8.6 Hz, 2H).

Aufarbeitung

  1. customThe solvent was evaporated
  2. additionwater (5 mL) was added
  3. filtrationThe mixture was filtered
  4. additionthe filtrate was made acidic to pH 3 by the addition of concentrated HCl
  5. filtrationThe precipitate was collected by filtration
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-17ed4ea8079545159d03b57ee05de260
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073881B2

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