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

HRID 1917156Notes

Reaction equation

HRID 1917156 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  1. filtrationthe resulting crystals were collected by vacuum filtration

Sources & evidence

ORD record
ord-c4358aa175404aecb09704c510ba2485
Source dataset
uspto-grants-2013_12
Patent number
US08618286B2

Reaction notes

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