Ethanol → 6-(3-Nitro-phenyl)-3H-benzothiazol-2-one

HRID 1007095

Reaction equation

HRID 1007095 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7](=[O:9])[S:8][C:4]=2[CH:3]=1.[N+:12]([C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13].C(=O)([O-])[O-].[K+].[K+].C(O)C>C1(C)C=CC=CC=1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C>[N+:12]([C:15]1[CH:20]=[C:19]([C:2]2[CH:11]=[CH:10][C:5]3[NH:6][C:7](=[O:9])[S:8][C:4]=3[CH:3]=2)[CH:18]=[CH:17][CH:16]=1)([O-:14])=[O:13]

Participants

9

Reactant 4

HCID 702EthanolHCID 16773-Nitrophenylboronic AcidHCID 11430Potassium CarbonateHCID 1884446-Bromo-2,3-dihydro-1,3-benzothiazol-2-one

Product 1

HCID 102211236-(3-Nitro-phenyl)-3H-benzothiazol-2-oneYield 1.8%

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 6-bromo-2-benzothiazolinone (5.0 g, 21.7 mmol), 3-nitrophenyl boronic acid (5.0 g, 30.0 mmol), tetrakis(triphenylphosphine)-palladium (0) (1.73 g, 1.5 mmol), and potassium carbonate (8.0 g, 58.0 mmol) in toluene (100 mL), H2O (20 mL), and ethanol (30 mL) was subject to a blanket of nitrogen for 15 minutes at 50° C. and then was heated at 85° C. for 24 hours. The reaction mixture was cooled to room temperature and ethyl acetate (100 mL) was added. The organic layer was washed with aqueous ammonium chloride (2×50 mL) and with brine (100 mL), dried over magnesium sulfate and concentrated. The residue was purified via chromatography (silica gel, 25% ethyl acetate/hexane) to give 6-(3-nitro-phenyl)-3H-benzothiazol-2-one as a brown solid (0.1 g, 1.8%): mp 276-277° C.; 1H-NMR (DMSO-d6) δ 11 (s, 1H), 8.44 (t, 1H, J=2.7 Hz), 8.21-8.08 (nm, 3H), 7.78-7.69 (m, 2H), 7.24 (d, 1H, J=9.23 Hz); MS (ES) m/z 271 ([M−H]−, 100%); Anal. Calc. For C13H8N2O3S 0.25 H2O: C, 56.41, H, 3.10, N, 10.12. Found: C, 56.48, H, 3.11, N, 9.99.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe organic layer was washed with aqueous ammonium chloride (2×50 mL) and with brine (100 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified via chromatography (silica gel, 25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-54480fa5e0044b458f328767e8111bb7
Source dataset
uspto-grants-2004_09
Patent number
US06794373B2

Linked notes

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