1-Bromo-4-(2-methylpropoxy)benzene → 2-Chloro-5-(4-isobutoxy-benzoyl)-benzenesulfonamide

HRID 873645ノート

反応式

HRID 873645 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1.C([Li])CCC.[Cl:18][C:19]1[CH:30]=[CH:29][C:22]([C:23](N(OC)C)=[O:24])=[CH:21][C:20]=1[S:31](=[O:34])(=[O:33])[NH2:32]>O1CCCC1>[Cl:18][C:19]1[CH:30]=[CH:29][C:22]([C:23](=[O:24])[C:2]2[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=2)=[CH:21][C:20]=1[S:31]([NH2:32])(=[O:34])=[O:33]

参加物

5

反応物 3

HCID 153241111-Bromo-4-(2-methylpropoxy)benzeneHCID 581073994-chloro-N-methoxy-N-methyl-3-sulfamoyl-benzamideHCID 178418339Butyllithium

生成物 1

HCID 442357412-Chloro-5-(4-isobutoxy-benzoyl)-benzenesulfonamide収率 37%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

1-Bromo-4-isobutoxy-benzene (625 mg, 2.73 mmol) is dissolved in tetrahydrofuran (2 mL) and cooled to −78° C. The solution is treated with a solution of n-butyllithium (1.6 M in hexanes, 1.7 mL, 2.73 mmol) and stirred 30 minutes after which a solution of 4-chloro-N-methoxy-N-methyl-3-sulfamoyl-benzamide (250 mg, 0.91 mmol) in tetrahydrofuran (2 mL) is added. The reaction is allowed to stir for 18 hours while warming to ambient temperature. The reaction is quenched with a saturated solution of ammonium chloride and extracted with ethyl acetate. The organic phase is separated and concentrated in vacuo. The residue is purified by column chromatography (gradient of ethyl acetate in hexanes 10-50%) affording 120 mg (37% yield) of the title compound. 1H NMR (DMSO) 1.00 (d, 6H, J=6.56 Hz), 2.01-2.10 (m, 1H), 3.88 (d, 2H, J=6.57 Hz), 7.11 (d, 2H, J=8.85 Hz), 7.76 (d, 2H, J=8.85 Hz), 7.81-7.84 (m, 3H), 7.89 (dd, 1H, J=2.02, 8.08), 8.24 (d, 1H, J=2.02). MS (m/z): 366 (M−1). CHN Calc C, 55.51; H, 4.93; N, 3.81. Found C, 55.38; H, 4.74; N, 3.77.

後処理

  1. additionis added
  2. temperaturewhile warming to ambient temperature
  3. customThe reaction is quenched with a saturated solution of ammonium chloride
  4. extractionextracted with ethyl acetate
  5. customThe organic phase is separated
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by column chromatography (gradient of ethyl acetate in hexanes 10-50%)

出典と根拠

ORDレコード
ord-165fc63980c840c4af5d5d4df7f142f2
出典データセット
uspto-grants-2015_03
特許番号
US08975439B2

反応ノート

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