Potassium Carbonate → 8-Bromo-2,2-dimethyl-2H-1,4-benzoxazin-3(4H)-one

HRID 1270099ノート

反応式

HRID 1270099 の反応式
Br[C:2]([CH3:15])([CH3:14])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[C:7]=1[OH:13])=[O:4].C([O-])([O-])=O.[K+].[K+].O.C(OCC)(=O)C>CN(C=O)C>[Br:12][C:8]1[C:7]2[O:13][C:2]([CH3:15])([CH3:14])[C:3](=[O:4])[NH:5][C:6]=2[CH:11]=[CH:10][CH:9]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 218735182-bromo-N-(3-bromo-2-hydroxy-phenyl)-2-methyl-propionamideHCID 22728543Water ethylacetate

生成物 1

HCID 218735118-Bromo-2,2-dimethyl-2H-1,4-benzoxazin-3(4H)-one収率 84.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
150 °C

実験手順

The 2-bromo-N-(3-bromo-2-hydroxy-phenyl)-2-methyl-propionamide of step 1 was dissolved in DMF (200 ml), and to the DMF solution was added to K2CO3 (6.3 g, 45.58 mmol). The mixture was heated overnight at 150° C., then cooled and poured into a mixture of water/ethyl acetate. The organic fraction was washed with brine. After drying over MgSO4, the organic fraction was concentrated in vacuo and resulting brown residue was purified by flash chromatography to give 8-bromo-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one as a white solid (84.6%). MS: (M−H)− 256.

後処理

  1. temperaturecooled
  2. washThe organic fraction was washed with brine
  3. dry with materialAfter drying over MgSO4
  4. concentrationthe organic fraction was concentrated in vacuo
  5. customresulting brown residue
  6. customwas purified by flash chromatography

出典と根拠

ORDレコード
ord-89a2c7c3c4004b8e8d01f4948e3b7480
出典データセット
uspto-grants-2007_04
特許番号
US07202241B2

反応ノート

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