Acetate → 6-Chloro-3-isothiocyanato-4-methylpyridazine

HRID 1398819ノート

反応式

HRID 1398819 の反応式
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[C:4]([CH3:9])[CH:3]=1.[C:10](Cl)(Cl)=[S:11].O.C([O-])(=O)C>C(=O)(O)[O-].[Na+].O1CCCC1>[Cl:1][C:2]1[N:7]=[N:6][C:5]([N:8]=[C:10]=[S:11])=[C:4]([CH3:9])[CH:3]=1

参加物

7

反応物 4

HCID 175AcetateHCID 962WaterHCID 10040ThiophosgeneHCID 123536646-Chloro-4-methylpyridazin-3-amine

生成物 1

HCID 866328736-Chloro-3-isothiocyanato-4-methylpyridazine収率 8.2%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of 6-chloro-4-methylpyridazin-3-amine (2.86 g, 20.0 mmol) in aqueous sodium bicarbonate (10 mL) and tetrahydrofuran (40 mL) was added thiophosgene (1.69 mL, 22.0 mmol) dropwise at 0° C. After stirring for 1 hr, water and ethyl, acetate were added to the mixture and the insoluble materials were filtered off. The filtrate was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the title compound (304 mg, 1.64 mmol, 8%) as a pale yellow solid.

後処理

  1. filtrationthe insoluble materials were filtered off
  2. washThe filtrate was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture
  6. concentrationThe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-a40b56ffdda44bd18a95220245db8f7f
出典データセット
uspto-grants-2014_12
特許番号
US08901141B2

反応ノート

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