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Methyl iodide → N-(2,4-dichloro-thiazol-5-yl)-N-methyl-3-methylsulfanyl-propionamide

HRID 1470445
ノート
印刷プレビュー

反応式

HRID 1470445 の反応式
[Cl:1][C:2]1[S:3][C:4]([NH:8][C:9](=[O:14])[CH2:10][CH2:11][S:12][CH3:13])=[C:5]([Cl:7])[N:6]=1.[C:15]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C.O>[Cl:1][C:2]1[S:3][C:4]([N:8]([CH3:15])[C:9](=[O:14])[CH2:10][CH2:11][S:12][CH3:13])=[C:5]([Cl:7])[N:6]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59580948N-(2,4-dichloro-thiazol-5-yl)-3-methylsulfanyl-propionamide

生成物 1

HCID 59580788N-(2,4-dichloro-thiazol-5-yl)-N-methyl-3-methylsulfanyl-propionamide収率 44%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6228
Dimethylformamide
溶媒

反応条件

温度
25 °C

実験手順

To a solution of N-(2,4-dichloro-thiazol-5-yl)-3-methylsulfanyl-propionamide (596 mg, 2.2 mmol) in DMF (11 mL) stirring at 25° C. was added K2CO3 (365 mg, 2.64 mmol) and iodomethane (375 mg, 1.2 mmol), the solution was stirred at 25° C. for 20 h. The solution was diluted with 50 mL H2O and extracted with ethyl acetate (3×20 mL). The combined organic extracts were washed with H2O (3×20 mL), dried over Na2SO4, filtered and concentrated to dryness under reduced pressure. The crude product was purified by silica gel chromatography (0 to 100% ethyl acetate/hexanes) to give the desired product as a clear oil (273 mg, 44%): 1H NMR (300 MHz, CDCl3) δ 3.23 (s, 3H), 2.79 (t, J=7.2 Hz, 2H), 2.52 (t, J=7.2 Hz, 2H), 2.09 (s, 3H); ESIMS m/z 285.1 (M+1).

後処理

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. washThe combined organic extracts were washed with H2O (3×20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe crude product was purified by silica gel chromatography (0 to 100% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-8616abbe984143e38cc29ae8cdb2139e
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09006446B2

反応ノート

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