Sodium Iodide → 7-Nitro-3,4-dihydro-2H-benzo[b][1,4]thiazine

HRID 424499Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 424499
Cl[CH2:2][CH2:3][S:4][C:5]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:6]=1[NH2:7].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C=O)C.O>[N+:12]([C:10]1[CH:9]=[CH:8][C:6]2[NH:7][CH2:2][CH2:3][S:4][C:5]=2[CH:11]=1)([O-:14])=[O:13]

Komponenten

6

Edukt 3

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 591440982-(2-Chloroethylthio)-4-nitroaniline

Produkt 1

HCID 204961217-Nitro-3,4-dihydro-2H-benzo[b][1,4]thiazineAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-(2-chloroethylthio)-4-nitroaniline (5.13 g, 22.05 mmol) in DMF (70 mL) was added potassium carbonate (9.14 g, 66.1 mmol), followed by sodium iodide (0.330 g, 2.205 mmol). The resulting suspension was stirred at room temperature overnight. The mixture was then diluted with water, and the resulting crystals were collected by vacuum filtration, giving the desired product (4.06 g, 94%). 1H NMR (DMSO-d6) δ 7.81-7.73 (m, 3H), 6.58 (t, J=9.0 Hz, 1H), 3.65-3.60 (m, 2H), 3.01-2.97 (m, 2H); ESI-MS (m/z, %): 197 (MH+, 100), 180 (99).

Aufarbeitung

  1. filtrationthe resulting crystals were collected by vacuum filtration

Quellen und Nachweise

ORD-Eintrag
ord-beec36693adb436fb38bf96dfbc99768
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106043B2

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