Water → 6-Isothiocyanato-2,4-dimethylnicotinonitrile

HRID 276244

反応式

HRID 276244 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]#[N:10])=[C:4]([CH3:11])[CH:3]=1.C([O-])([O-])=O.[Ca+2].O.[C:18](Cl)(Cl)=[S:19]>C(Cl)Cl>[CH3:8][C:6]1[C:5]([C:9]#[N:10])=[C:4]([CH3:11])[CH:3]=[C:2]([N:1]=[C:18]=[S:19])[N:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 10040ThiophosgeneHCID 10112Calcium CarbonateHCID 37932996-Amino-2,4-dimethyl-3-pyridinecarbonitrile

生成物 1

HCID 183162016-Isothiocyanato-2,4-dimethylnicotinonitrile収率 93.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

A suspension of 6-amino-3-cyano-2,4-dimethylpyridine (0.1 g, 0.68 mmol) in CH2Cl2 (1 mL) was added to a vigorously stirred mixture of CaCO3 (0.41 g, 4.11 mmol) in a 1:2 water:CH2Cl2 mixture (9 mL total) at room temp. The reaction mixture was cooled to 0° C. and thiophosgene (0.09 g, 0.78 mmol) was added dropwise. The resulting mixture was allowed to warm to room temp and was stirred overnight. The resulting aqueous layer was back-extracted with CH2Cl2 (3×10 mL). The combined organic layers were washed with water (10 mL), dried (MgSO4) and concentrated under reduced pressure. The residue was purified by chromatography (SiO2, 10% EtOAc/hex) to give 2,4-dimethyl-3-cyano-6-pyridyl isothiocyanate (0.12 g, 91%): CI-MS m/z 190 ((M+H)+).

後処理

  1. customat room temp
  2. temperatureto warm to room temp
  3. extractionThe resulting aqueous layer was back-extracted with CH2Cl2 (3×10 mL)
  4. washThe combined organic layers were washed with water (10 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography (SiO2, 10% EtOAc/hex)

出典と根拠

ORDレコード
ord-2e90a8d951224d7f91b9854854bc5ed9
出典データセット
uspto-grants-2002_03
特許番号
US06353006B1

関連ノート

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