Potassium Iodide → 7-Bromo-5-iodo-benzo[d]isothiazole

HRID 389471ノート

反応式

HRID 389471 の反応式
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:13][C:14]1[C:22]2[S:21][N:20]=[CH:19][C:18]=2[CH:17]=[C:16](N)[CH:15]=1.N([O-])=O.[Na+].[I-:28].[K+].C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C.O>[Br:13][C:14]1[C:22]2[S:21][N:20]=[CH:19][C:18]=2[CH:17]=[C:16]([I:28])[CH:15]=1

参加物

9

反応物 6

HCID 4875Potassium IodideHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 23668193Sodium NitriteHCID 667606927-Bromo-benzo[d]isothiazol-5-ylamine

生成物 1

HCID 667603867-Bromo-5-iodo-benzo[d]isothiazole収率 50.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6342Acetonitrile溶媒

反応条件

温度
12.5 °C

実験手順

To a solution of p-toluenesulfonic acid monohydrate (1.36 g, 7.2 mmol) in acetonitrile (8.5 mL) was added 7-bromo-benzo[d]isothiazol-5-ylamine (400 mg, 1.74 mmol). The resulting suspension was cooled to 10 to 15° C. and a solution of sodium nitrite (331 mg, 4.8 mmol) and potassium iodide (996 mg, 6 mmol) in water (1.5 mL) was added gradually. The reaction mixture was stirred for 10 min and then allowed to come to RT and stirred for 16 h. The reaction mixture was treated with water (5 mL) and aqueous 1.0 N sodium bicarbonate solution (15 mL), and aqueous 2.0 N sodium thiosulfate solution (10 mL). The precipitate was collected by filtration and the purified by column chromatography (25% ethyl acetate:hexanes) to afford 300 mg (50%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 8.9 (s, 1H), 8.37 (d, J=1.2 Hz, 1H), 7.91 (d, J=1.5 Hz, 1H).

後処理

  1. customto come to RT
  2. stirringstirred for 16 h
  3. filtrationThe precipitate was collected by filtration
  4. customthe purified by column chromatography (25% ethyl acetate:hexanes)

出典と根拠

ORDレコード
ord-f481fbab4ed7496d81a52a1b172b26e5
出典データセット
uspto-grants-2013_02
特許番号
US08378104B2

反応ノート

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