N-bromobutanimide → [2-Amino-4-(4-fluoro-phenyl)-thiazol-5-yl]-(4-fluoro-phenyl)-methanone

HRID 2368426

Reaktionsgleichung

Reaktionsgleichung von HRID 2368426
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[O:11])=[CH:4][CH:3]=1.C1C(=O)N(Br)C(=O)C1.[NH2:28][C:29]([NH2:31])=[S:30]>C(O)C>[NH2:31][C:29]1[S:30][C:9]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[O:11])=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[N:28]=1

Komponenten

5

Edukt 3

HCID 67184N-bromobutanimideHCID 738961,3-Propanedione, 1,3-bis(4-fluorophenyl)-HCID 2723790Thiourea

Produkt 1

HCID 14435315[2-Amino-4-(4-fluoro-phenyl)-thiazol-5-yl]-(4-fluoro-phenyl)-methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

1,3-Bis-(4-fluoro-phenyl)-propane-1,3-dione and NBS (1.05 eq) were heated neat at 60° C. for 10 minutes then cooled. The resulting mixture was dissolved in ethanol (0.2 M) and treated with thiourea (1.5 eq). It was heated at reflux for 15 hours and cooled to room temperature. It was evaporated to dryness and the residue was partioned between EtOAc and saturated NaHCO3. Organic fraction was dried over MgSO4, filtered and concentrated. The title compound was collected by trituration with heptanes. 1H NMR (400 MHz, DMSO-d6) 6.86-7.01 (m, 4H) 7.22-7.32 (m, 2H) 7.35-7.45 (m, 2H) 8.11 (br. s., 2H). LCMS Method A Rt=1.18 m/z 317.0 (M+1), 315 (M−1).

Aufarbeitung

  1. temperaturethen cooled
  2. temperatureIt was heated
  3. temperatureat reflux for 15 hours
  4. customIt was evaporated to dryness
  5. dry with materialOrganic fraction was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe title compound was collected by trituration with heptanes

Quellen und Nachweise

ORD-Eintrag
ord-1c576a8d17c5455bb136cf2ff0fd0853
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703761B2

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