Sodium Bicarbonate → 6-(2-Thienyl)-2-methyl-1,4-benzoxazin-3-(4h)-one

HRID 840369Notes

Reaction equation

HRID 840369 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]([CH3:11])[C:8](=[O:12])[NH:7][C:6]=2[CH:13]=1.[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1B(O)O.C(=O)(O)[O-].[Na+]>COCCOC.C(OCC)(=O)C>[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]([CH3:11])[C:8](=[O:12])[NH:7][C:6]=2[CH:13]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 27339602-Thiopheneboronic acidHCID 226229036-bromo-2-methyl-3,4-dihydro-2H-1,4-benzoxazin-3-one

Product 1

HCID 226229196-(2-Thienyl)-2-methyl-1,4-benzoxazin-3-(4h)-oneYield 33%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

315 mg of 6-bromo-2-methyl-1,4-benzoxazin-3-(4H)-one is mixed in 4 ml of DME with 0.2 g of 2-thiopheneboronic acid and 150 mg of tetrakis-triphenylphosphine-palladium (O) and 340 mg of sodium bicarbonate (dissolved in 4 ml of water). It is stirred for some time at 100° C. The product is diluted with ethyl acetate, extracted 3 times with water, and dried with magnesium sulfate. It is concentrated by evaporation. The crude product is purified by column chromatography with a hexane/ethyl acetate mixture and yields pure 33% product.

Workup

  1. extractionextracted 3 times with water
  2. dry with materialdried with magnesium sulfate
  3. concentrationIt is concentrated by evaporation
  4. customThe crude product is purified by column chromatography with a hexane/ethyl acetate mixture

Sources & evidence

ORD record
ord-32bf2a6a5f0846fb80338bb81efe33f4
Source dataset
uspto-grants-2002_04
Patent number
US06365736B1

Reaction notes

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