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

HRID 1917156Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1917156
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-c4358aa175404aecb09704c510ba2485
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618286B2

Notizen zur Reaktion

Wird geladen…