Sulfuric Acid → 3-Cyclopropyl-5-iodoisothiazole

HRID 2173016ノート

反応式

HRID 2173016 の反応式
[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

参加物

8

反応物 5

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

生成物 1

HCID 711438323-Cyclopropyl-5-iodoisothiazole収率 40%

試薬・触媒・溶媒 2

HCID 962Water溶媒3 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-67cfe5c992aa4fc5b08ecfec0c6834bb
出典データセット
uspto-grants-2015_06
特許番号
US09056873B2

反応ノート

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