Potassium Iodide → N-Methyl-3-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)propan-1-amine

HRID 424547Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 424547
Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][S:8][C:7]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:6]1=2.Cl.[CH3:19][NH2:20].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[CH3:19][NH:20][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][S:8][C:7]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:6]1=2

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 6364545Methylamine hydrochlorideHCID 591440694-(3-Chloropropyl)-7-nitro-3,4-dihydro-2H-benzo[b][1,4]thiazine

Produkt 1

HCID 59144086N-Methyl-3-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)propan-1-amineAusbeute 74,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 4-(3-chloropropyl)-7-nitro-3,4-dihydro-2H-benzo[b][1,4]thiazine (1.1 g, 4.03 mmol), methylamine hydrochloride (0.545 g, 8.07 mmol), potassium iodide (0.669 g, 4.03 mmol), and potassium carbonate (2.79 g, 20.16 mmol) in dry acetonitrile (25 mL) was stirred at 80° C. in a sealed tube for 6 hours. The reaction was brought to room temperature and diluted with water (100 mL), and the product was extracted into ethyl acetate (3×25 mL). The combined ethyl acetate layers were washed with brine (20 mL) and dried (Na2SO4). The solvent was evaporated, and the crude material was purified by flash column chromatography (1:9 (2M NH3 in MeOH):CH2Cl2) on silica gel to obtain the title compound (0.8 g, 74%) as a thick syrup. 1H NMR (DMSO-d6) δ 7.84-7.81 (m, 2H), 6.86 (d, 1H, J=9.9 Hz), 3.78-3.75 (m, 2H), 3.50 (t, 2H, J=7.5 Hz), 3.08-3.04 (m, 2H), 2.48 (t, 2H, J=6.9 Hz), 2.27 (s, 3H), 1.74-1.64 (m, 2H); ESI-MS (m/z, %): 268 (MH+, 100).

Aufarbeitung

  1. customwas brought to room temperature
  2. extractionthe product was extracted into ethyl acetate (3×25 mL)
  3. washThe combined ethyl acetate layers were washed with brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated
  6. customthe crude material was purified by flash column chromatography (1:9 (2M NH3 in MeOH):CH2Cl2) on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-d0648734ce654422b0208ee06ad4bba6
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106043B2

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