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

HRID 389471노트

반응식

HRID 389471 반응식
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

참가 물질

9

반응물 6

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 6342Acetonitrile용매

반응 조건

온도
12.5 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f481fbab4ed7496d81a52a1b172b26e5
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08378104B2

반응 노트

불러오는 중…