Potassium Carbonate → 6-Nitro-3,4-dihydro-2H-benzo[b][1,4]thiazine

HRID 424553Notes

Reaction equation

HRID 424553 reaction equation
I[CH2:2][CH2:3][S:4][C:5]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:6]=1[NH2:7].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[N+:12]([C:9]1[CH:10]=[CH:11][C:5]2[S:4][CH2:3][CH2:2][NH:7][C:6]=2[CH:8]=1)([O-:14])=[O:13]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 59144079HCID 59144079, compound

Product 1

HCID 457916016-Nitro-3,4-dihydro-2H-benzo[b][1,4]thiazineYield 87.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 2-(2-iodoethylthio)-5-nitroaniline (1.18 g, 3.64 mmol) in DMF (10 mL) was added potassium carbonate (1.006 g, 7.28 mmol). The resulting mixture was then stirred at 90° C. for 1 hour. The mixture was then cooled to room temperature and diluted with water (40 mL). The resulting red precipitate was collected by vacuum filtration, giving the title compound (625 mg, 87%). 1H NMR (DMSO-d6) δ 7.38 (s, 1H), 7.28 (d, J=8.4 Hz, 1H), 7.12 (d, J=8.7 Hz, 6.78 (brs, 1H), 3.56-3.49 (m, 2H), 3.08-3.03 (m, 2H); EI-MS (m/z, %): 196 (M+, 100), 181 (45), 122 (73).

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. filtrationThe resulting red precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-274ab1a04e684f44972b6f02a584ad98
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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