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Sodium Thiosulfate → Methyl 2-(methylsulfonyl)pyrimidine-5-carboxylate

HRID 2381961
ノート
印刷プレビュー

反応式

HRID 2381961 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8](SC)=[N:9][CH:10]=1)=[O:4].[CH:13]1C=C(Cl)C=C(C(OO)=O)C=1.[O-:24][S:25]([O-:28])(=S)=O.[Na+].[Na+]>C(Cl)Cl.O>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([S:25]([CH3:13])(=[O:28])=[O:24])=[N:7][CH:6]=1)=[O:4]
参加物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 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 11194721Methyl 2-(Methylthio)pyrimidine-5-carboxylate

生成物 1

HCID 53396491Methyl 2-(methylsulfonyl)pyrimidine-5-carboxylate収率 90%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344
Dichloromethane
溶媒

実験手順

To a solution of 2-methylsulfanyl-pyrimidine-5-carboxylic acid methyl ester (1 g, 5.43 mmol) in DCM (60 mL) is added MCPBA (2.81 g, 16.29 mmol) portion wise at rt. The resulting solution is stirred at rt overnight. A solution of Na2S2O3 (1.6 g) in water (60 mL) is added. The mixture is stirred at rt for 20 min. The organic layer and aqueous layer are separated, and the aqueous layer is extracted with DCM (2×20 mL). The combined organic layer is washed with saturated aqueous NaHCO3 (3×20 mL), dried (Na2SO4), filtered and concentrated in vacuo to afford 2-methanesulfonyl-pyrimidine-5-carboxylic acid methyl ester (1.05 g, 90%) as a solid. MS: 217 (M+H); 1H NMR (300 MHz, CDCl3): δ 3.41 (s, 3H), 4.06 (s, 3H), 9.44 (s, 2H).

後処理

  1. stirringThe mixture is stirred at rt for 20 min
  2. customThe organic layer and aqueous layer are separated
  3. extractionthe aqueous layer is extracted with DCM (2×20 mL)
  4. washThe combined organic layer is washed with saturated aqueous NaHCO3 (3×20 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-c2fbc95ae24245038e7ce9692163b307
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08258130B2

反応ノート

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