Water → 4-Methyl-6-(methylsulfonyl)pyridin-3-amine

HRID 1811567

反応式

HRID 1811567 の反応式
Cl[C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[C:4]([CH3:9])[CH:3]=1.[CH3:10][S:11]([O-:13])=[O:12].[Na+].CNCCNC.O>[Cu].CS(C)=O>[CH3:10][S:11]([C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[C:4]([CH3:9])[CH:3]=1)(=[O:13])=[O:12]

参加物

7

反応物 4

HCID 962WaterHCID 8070N,N'-DimethylethylenediamineHCID 2733271Sodium methanesulfinateHCID 27344253-Amino-6-chloro-4-picoline

生成物 1

HCID 586715824-Methyl-6-(methylsulfonyl)pyridin-3-amine収率 27%

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
150 °C

実験手順

A mixture of 6-chloro-4-methyl-pyridin-3-ylamine (1.53 g, 11 mmol), sodium methanesulfinate (1.60 g, 16 mmol), copper catalyst (0.50 g, 0.99 mmol), and N1,N2-dimethylethane-1,2-diamine (0.214 mL, 2.0 mmol) in 20 mL DMSO was heated under microwave irradiation at 150° C. After 2 h, mixture was poured into ca. 200 mL water and extracted five times with ca. 200 mL AcOEt. Organic phases were dried over MgSO4, filtered, and concentrated. Residue was purified by column chromatography (AcOEt/hexane 5:1→AcOEt) to give 6-methanesulfonyl-4-methyl-pyridin-3-ylamine as a white solid (0.534 g, 27%). 1HNMR (DMSO-d6, 400 MHz) 32.4 (s, 3H), 3.08 (s, 3H), 6.08 (s, 2H), 7.59 (s, 1H), 7.97 (s, 1H). Exact mass calculated for C7H10N2O2S 186.05 found 187.0 (MH+).

後処理

  1. extractionextracted five times with ca. 200 mL AcOEt
  2. dry with materialOrganic phases were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customResidue was purified by column chromatography (AcOEt/hexane 5:1→AcOEt)

出典と根拠

ORDレコード
ord-b197c6bfbf21446cb32f5e377ae6ff9e
出典データセット
uspto-grants-2013_01
特許番号
US08362248B2

関連ノート

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