Sodium Iodide → Methyl 4,5,6-trichloro-3-iodopicolinate

HRID 75090ノート

反応式

HRID 75090 の反応式
N[C:2]1[C:3]([C:11]([O:13][CH3:14])=[O:12])=[N:4][C:5]([Cl:10])=[C:6]([Cl:9])[C:7]=1[Cl:8].N([O-])=O.[Na+].[I-:19].[Na+].S(=O)(O)[O-].[Na+]>Cl.O.ClCCl.C(OCC)(=O)C>[Cl:8][C:7]1[C:6]([Cl:9])=[C:5]([Cl:10])[N:4]=[C:3]([C:11]([O:13][CH3:14])=[O:12])[C:2]=1[I:19]

参加物

9

反応物 4

HCID 5238Sodium IodideHCID 23665763Sodium BisulfiteHCID 23668193Sodium NitriteHCID 86668297Methyl 3-amino-4,5,6-trichloropicolinate

生成物 1

HCID 86668296Methyl 4,5,6-trichloro-3-iodopicolinate収率 245.7%

試薬・触媒・溶媒 4

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
5 °C

実験手順

Methyl 3-amino-4,5,6-trichloropicolinate (0.5 g, 2.0 mmol) was dissolved in concentrated HCl (20 mL), cooled to 5° C., and treated with a solution of sodium nitrite (0.2 g, 3.0 mmol dissolved in 1 mL of water) over 15 minutes. The reaction mixture was stirred for 20 minutes at 5° C. and poured carefully into a rapidly stirred mixture of sodium iodide (1.8 g; 12 mmol) in water (100 mL) and dichloromethane (30 mL). After 20 minutes, solid sodium bisulfite was added. Ethyl acetate (100 mL) was added and the phases were separated. The organic phase was washed with saturated sodium chloride, dried over sodium sulfate, and concentrated under vacuum. The above procedure was performed again on 1.5 g of the amine and the combined crude products were purified by flash chromatography (SiO2, hexane/ethyl acetate) to afford the title compound as a white solid (1.8 g 61%): mp 61-62° C.; 1H NMR (400 MHz, CDCl3) δ 4.00 (s, 3H); EIMS m/z 365.

後処理

  1. waitAfter 20 minutes
  2. customthe phases were separated
  3. washThe organic phase was washed with saturated sodium chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customthe combined crude products were purified by flash chromatography (SiO2, hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-cdc52720d8254228bab9f796347abf31
出典データセット
uspto-grants-2014_09
特許番号
US08835409B2

反応ノート

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