Hydrazine hydrate (1:1) → 2-{2-[(4-Bromophenyl)sulfonyl]phenyl}-1,3,4-oxadiazole

HRID 2376999

反応式

HRID 2376999 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=2[C:13]([O:15][CH3:16])=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.O.[NH2:22][NH2:23]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=2[C:13]2[O:15][CH:16]=[N:22][N:23]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

参加物

3

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 21099525Methyl 2-[(4-bromophenyl)sulfonyl]benzoate

生成物 1

HCID 210994102-{2-[(4-Bromophenyl)sulfonyl]phenyl}-1,3,4-oxadiazole収率 35.7%

反応条件

温度
90 °C

実験手順

Methyl 2-[(4-bromophenyl)sulfonyl]benzoate (Example 144 Step 1; 150 mg, 0.46 mmol) and hydrazine hydrate (0.06 mL, 2.32 mmol) were stirred together at room temperature for 1.5 h then at 90° C. for 2 h. The excess hydrazine was removed in vacuo and the residue was dissolved in triethylorthoformate (4.6 mL) with catalytic camphorsulfonic acid and the mixture heated at 90° C. overnight. The cooled reaction mixture was partitioned between EtOAc and water and the organic layer was washed with brine and evaporated in vacuo. The residue was purified by flash column chromatography on silica (eluant 50% EtOAc/isohexane) to yield 2-{2-[(4-bromophenyl)sulfonyl]phenyl}-1,3,4-oxadiazole (60 mg, 35%). δH (400 MHz, d6 DMSO): 9.42 (1H, s), 8.35-8.33 (1H, m), 7.97-7.91 (2H, m), 7.86-7.84 (3H, m), 7.80-7.78 (2H, m).

後処理

  1. customThe excess hydrazine was removed in vacuo
  2. dissolutionthe residue was dissolved in triethylorthoformate (4.6 mL) with catalytic camphorsulfonic acid
  3. customThe cooled reaction mixture
  4. customwas partitioned between EtOAc and water
  5. washthe organic layer was washed with brine
  6. customevaporated in vacuo
  7. customThe residue was purified by flash column chromatography on silica (eluant 50% EtOAc/isohexane)

出典と根拠

ORDレコード
ord-61a59ad759c54e2cbaa1ca8890e43f97
出典データセット
uspto-grants-2008_12
特許番号
US07468393B2

関連ノート

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