Phenacyl bromide → (3,4-Dichloro-phenyl)-(4-phenyl-thiazol-2-yl)-amine

HRID 130350

Reaktionsgleichung

Reaktionsgleichung von HRID 130350
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH2:12])=[S:11])[CH:5]=[CH:6][C:7]=1[Cl:8].Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=O>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[S:11][CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:12]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Komponenten

4

Edukt 2

HCID 6259Phenacyl bromideHCID 710776N-(3,4-Dichlorophenyl)thiourea

Produkt 1

HCID 86228547(3,4-Dichloro-phenyl)-(4-phenyl-thiazol-2-yl)-amineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To (3,4-Dichloro-phenyl)-thiourea (2 g, 9.04 mmol) in ethanol (35 mL) was added 2-Bromo-1-phenyl-ethanone and the solution was refluxed overnight. The reaction mixture was allowed to cool to room temperature and the resulting solid was filtered and washed with cold ethyl acetate to yield 2.45 g (85%) of an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ 8.16 (d, J=1.8 Hz, 1H), 7.87 (d, J=7.5 Hz, 2 H), 7.61-7.29 (m, 6H); LCMS m/z 319 [M−1]

Aufarbeitung

  1. temperaturethe solution was refluxed overnight
  2. filtrationthe resulting solid was filtered
  3. washwashed with cold ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-8a202ee4d2fb468b8ed0a91ab4595007
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381736B2

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