Sulfuric Acid → 3-Cyclopropyl-5-iodoisothiazole

HRID 2173016노트

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HRID 2173016 반응식
[CH:1]1([C:4]2[CH:8]=[C:7](N)[S:6][N:5]=2)[CH2:3][CH2:2]1.S(=O)(=O)(O)O.N([O-])=O.[Na+].[I-:19].[K+].C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C>[CH:1]1([C:4]2[CH:8]=[C:7]([I:19])[S:6][N:5]=2)[CH2:3][CH2:2]1

참가 물질

8

반응물 5

HCID 1118Sulfuric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 23668193Sodium NitriteHCID 451166973-Cyclopropylisothiazol-5-amine

생성물 1

HCID 711438323-Cyclopropyl-5-iodoisothiazole수율 40%

시약·촉매·용매 2

HCID 962Water용매3회HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

To a water (1.4 mL) and ice (5.0 cc) suspension was added 3-cyclopropylisothiazol-5-amine (500 mg, 3.57 mmol) followed by concentrated sulfuric acid (1.4 mL). A solution of sodium nitrite (258 mg, 3.74 mmol) in water (5.0 mL) was added dropwise at 0° C., and the mixture was stirred at 0° C. for 1 hour. Next, a solution of potassium iodide (622 mg, 3.74 mmol) in water (3.5 mL) was added dropwise at 0° C., and the mixture was heated at 80° C. for 1 hour. Ethyl acetate at 0° C. was added and the mixture was neutralized with potassium carbonate. The organic layer was separated, dried over magnesium sulfate, concentrated under reduced pressure, and purified by silica gel chromatography (Flash 60 column) eluting with hexane/EtOAc (19:1) to give the title compound as green oil (356.5 mg, 40%). 1H NMR (500 MHz, CDCl3) δ ppm 0.92-0.98 (m, 2H), 0.98-1.04 (m, 2H), 2.13-2.20 (m, 1H), 7.06 (s, 1H).

후처리

  1. temperaturethe mixture was heated at 80° C. for 1 hour
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. custompurified by silica gel chromatography (Flash 60 column)
  6. washeluting with hexane/EtOAc (19:1)

출처 및 근거

ORD 기록
ord-67cfe5c992aa4fc5b08ecfec0c6834bb
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056873B2

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