Methylamine tetrahydrofuran → 4-(4-bromo-3,5-dimethoxyphenyl)-1-methyl-1H-imidazole

HRID 56501

反応式

HRID 56501 の反応式
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([CH:10]2O[CH:13]=[N:12][CH:11]2S(C2C=CC(C)=CC=2)(=O)=O)=[CH:4][C:3]=1[O:25][CH3:26].[CH3:27][NH2:28].C1COCC1>CO.CCOC(C)=O>[Br:1][C:2]1[C:3]([O:25][CH3:26])=[CH:4][C:5]([C:10]2[N:28]=[CH:27][N:12]([CH3:13])[CH:11]=2)=[CH:6][C:7]=1[O:8][CH3:9]

参加物

4

反応物 2

HCID 66615946Methylamine tetrahydrofuranHCID 673894555-(4-Bromo-3,5-dimethoxyphenyl)-4-tosyl-4,5-dihydrooxazole

生成物 1

HCID 584319944-(4-bromo-3,5-dimethoxyphenyl)-1-methyl-1H-imidazole収率 21%

試薬・触媒・溶媒 1

HCID 21584119Ethylacetate methanol溶媒

反応条件

温度
135 °C

実験手順

To an oven-dried pressure tube was added 5-(4-bromo-3,5-dimethoxyphenyl)-4-tosyl-4,5-dihydrooxazole (0.4 g, 0.91 mmol), methylamine-THF solution (1.8 mL of a 2.0 M solution, 3.6 mmol), and xylenes (5 mL). The tube was sealed under argon then heated at 135° C. for 15 hours. After cooling to room temperature, the reaction mixture was transferred and concentrated in vacuo then partitioned between EtOAc and H2O. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organics were washed with brine twice, dried over Na2SO4 and concentrated. Purification by chromatography (50-100% EtOAc-hexanes then 2-5% MeOH-EtOAc) provided 4-(4-bromo-3,5-dimethoxyphenyl)-1-methyl-1H-imidazole as a light yellow solid (0.056 g, 21% yield).

後処理

  1. customThe tube was sealed under argon
  2. temperatureAfter cooling to room temperature
  3. concentrationconcentrated in vacuo
  4. customthen partitioned between EtOAc and H2O
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with EtOAc
  7. washThe combined organics were washed with brine twice
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customPurification by chromatography (50-100% EtOAc-hexanes

出典と根拠

ORDレコード
ord-fccd77aced164354bdf2c464291341cf
出典データセット
uspto-grants-2016_09
特許番号
US09434707B2

関連ノート

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