3-Nitrophenylboronic Acid → 7-(3-nitro-phenyl)-4H-benzo[1,4]thiazin-3-one

HRID 1007098Notes

Reaction equation

HRID 1007098 reaction equation
Br[C:2]1[CH:12]=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][S:9][C:4]=2[CH:3]=1.[N+:13]([C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1)([O-:15])=[O:14].C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.C(O)C.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>[N+:13]([C:16]1[CH:21]=[C:20]([C:2]2[CH:12]=[CH:11][C:5]3[NH:6][C:7](=[O:10])[CH2:8][S:9][C:4]=3[CH:3]=2)[CH:19]=[CH:18][CH:17]=1)([O-:15])=[O:14]

Participants

8

Reactant 3

HCID 16773-Nitrophenylboronic AcidHCID 11430Potassium CarbonateHCID 6890657-Bromo-2H-(1,4)-benzothiazin-3(4h)-one

Product 1

HCID 98823337-(3-nitro-phenyl)-4H-benzo[1,4]thiazin-3-one

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 7-bromo-4H-benzo[1,4]thiazin-3-one (2 g, 8.2 mmol), 3-nitrophenyl boronic acid (2.72 g, 16.4 mmol), potassium carbonate (6.85 g, 49.2 mmol), and tetrakis(triphenylphosphine) palladium(0) (0.95 g, 0.82 mmol) in dimethoxyethane (100 ml), ethanol (25 ml), and water (25 ml) was heated to reflux for 6 hours. After cooling to room temperature, the mixture was diluted with water and extracted with EtOAc (3×50 mL). The combined organic extracts were washed with water, then brine, dried (MgSO4) and evaporated to obtain crude 7-(3-nitro-phenyl)-4H-benzo[1,4]thiazin-3-one (0.15 g, 6%). Recrystallization of crude sample from EtOAc afforded the title compound: mp 290-292° C.; MS (EI) m/z 286 (M30).

Workup

  1. temperatureto reflux for 6 hours
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe combined organic extracts were washed with water
  4. dry with materialbrine, dried (MgSO4)
  5. customevaporated
  6. customto obtain crude 7-(3-nitro-phenyl)-4H-benzo[1,4]thiazin-3-one (0.15 g, 6%)
  7. customRecrystallization of crude sample from EtOAc

Sources & evidence

ORD record
ord-267e830b002a40358132a8298ddf2105
Source dataset
uspto-grants-2004_09
Patent number
US06794373B2

Reaction notes

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