Sodium Iodide → 3-Chloro-4-(thiazol-4-ylmethoxy)-phenylamine hydrochloride

HRID 2353819Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2353819
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[OH:11].Cl.Cl[CH2:14][C:15]1[N:16]=[CH:17][S:18][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C.C(Cl)Cl.O>[ClH:1].[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[O:11][CH2:14][C:15]1[N:16]=[CH:17][S:18][CH:19]=1

Komponenten

8

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 12074NitrofunginHCID 27632894-(Chloromethyl)-1,3-thiazole hydrochloride

Produkt 1

HCID 673132263-Chloro-4-(thiazol-4-ylmethoxy)-phenylamine hydrochlorideAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-4-nitrophenol (1.00 g, 5.76 mmol) in acetonitrile (125 mL) were added 4-chloromethylthiazole hydrochloride (1.08 g, 6.34 mmol), Potassium carbonate (2.39 g, 17.29 mmol) and sodium iodide (1.73 g, 11.52 mmol). The reaction mixture was stirred at 60 C overnight. Water (60 mL) and DCM (10 mL) were added. After all solid material dissolved, layers formed were separated. The organic layer was washed with water and brine, dried over Na2SO4 and concentrated down to give the required material as a light yellow solid (1.29 mg, 83%). 1H-NMR (CD2Cl2) δ 8.87 (d, 1H), 8.32 (d, 1H), 8.16 (dd, 1H), 7.54-7.56 (m, 1H), 7.22 (d, 1H), 5.33-5.34 (m, 2H); LCMS RT=3.01 min; [M+H]+=271.0.

Aufarbeitung

  1. dissolutionAfter all solid material dissolved
  2. customlayers formed
  3. customwere separated
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated down

Quellen und Nachweise

ORD-Eintrag
ord-d4aa5a7bbf1c42648a0fb93a0ecf77b8
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07750017B2

Notizen zur Reaktion

Wird geladen…