Water → methyl 5-(N-(2,4-dimethylphenyl)-N-isobutylsulfamoyl)-2-hydroxybenzoate

HRID 1487074ノート

反応式

HRID 1487074 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:25][CH:26]([CH3:28])[CH3:27])[S:10]([C:13]1[CH:14]=[CH:15][C:16]([O:23]C)=[C:17]([CH:22]=1)[C:18]([O:20][CH3:21])=[O:19])(=[O:12])=[O:11].B(Br)(Br)Br.O>ClCCl>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:25][CH:26]([CH3:28])[CH3:27])[S:10]([C:13]1[CH:14]=[CH:15][C:16]([OH:23])=[C:17]([CH:22]=1)[C:18]([O:20][CH3:21])=[O:19])(=[O:12])=[O:11]

参加物

5

反応物 3

HCID 962WaterHCID 25134Boron tribromideHCID 89875889methyl 5-(N-(2,4-dimethylphenyl)-N-isobutylsulfamoyl)-2-methoxybenzoate

生成物 1

HCID 89875696methyl 5-(N-(2,4-dimethylphenyl)-N-isobutylsulfamoyl)-2-hydroxybenzoate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

Methyl 5-(N-(2,4-dimethylphenyl)-N-isobutylsulfamoyl)-2-methoxybenzoate (1.485 g, 3.66 mmol) was dissolved in dichloromethane (DCM) (10 mL) and this was cooled to −78° C. A solution of boron tribromide in DCM (1M, 18.31 mL, 18.31 mmol) was then added dropwise and the reaction stirred under nitrogen. The reaction was then allowed to warm to room temperature and stirred overnight. Water (20 mL) was added dropwise to the reaction mixture and the crude product extracted to the organic phase of an aqueous work up between DCM and water. The aqueous phase was washed twice with DCM. The organic phase was then dried and concentrated in vacuo to give the crude product. LCMS [LCMS2] Rt 1.42 min, m/z (ES+) 392 (M+H).

後処理

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. extractionthe crude product extracted to the organic phase of an aqueous work up between DCM and water
  4. washThe aqueous phase was washed twice with DCM
  5. customThe organic phase was then dried
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-05a66b9b55054b119c792b705211e1fe
出典データセット
uspto-grants-2016_08
特許番号
US09428452B2

反応ノート

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