Dichloromethane → 2-(4'-Amino-3'-iodophenyl)-6-methoxybenzothiazole

HRID 2039386

Reaktionsgleichung

Reaktionsgleichung von HRID 2039386
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[I:19]Cl.C(Cl)Cl>C(O)(=O)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:6][C:7]=1[I:19]

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 24640Iodine chlorideHCID 3918704-(6-Methoxy-1,3-benzothiazol-2-yl)aniline

Produkt 1

HCID 100684372-(4'-Amino-3'-iodophenyl)-6-methoxybenzothiazoleAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 2-(4′-aminophenyl)-6-methoxy benzothiazole (22 mg, 0.09 mmol) in glacial acetic acid (2.0 mL) was injected 1 M iodochloride solution in CH2Cl2 (0.10 mL, 0.10 mmol, 1.2 eq.) under N2 atmosphere. The reaction mixture was stirred at room temperature for 16 hr. The glacial acetic acid was removed under reduced pressure and the residue was dissolved in CH2Cl2. After neutralizing the solution with NaHCO3, the aqueous layer was separated and extracted with CH2Cl2. The organic layers were combined and dried over MgSO4. Following the evaporation of the solvent, the residue was purified by preparative TLC(Hexanes:ethyl acetate=6:1) to give 2-(4′-amino-3′-iodophenyl)-6-methoxy benzothiazole (25 mg, 76%) as brown solid. 1HNMR (300 MHz, CDCl3) δ (ppm): 8.35 (d, J=2.0 Hz, 1H), 7.87 (dd, J1=2.0 Hz, J2=9.0 Hz, 1H), 7.31 (d, J=2.2 Hz, 1H), 7.04 (dd, J1=2.2 Hz, J2=9.0 Hz, 1H), 6.76 (d, J=9.0 Hz, 1H), 3.87 (s, 3H).

Aufarbeitung

  1. customThe glacial acetic acid was removed under reduced pressure
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. customthe aqueous layer was separated
  4. extractionextracted with CH2Cl2
  5. dry with materialdried over MgSO4
  6. customthe evaporation of the solvent
  7. customthe residue was purified by preparative TLC(Hexanes:ethyl acetate=6:1)

Quellen und Nachweise

ORD-Eintrag
ord-03cf2e9e9f8148b487b180bfcbfbd17d
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580229B2

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