3-Chloro-4-nitrophenol → 2-Methylsulfanyl-4-(3-chloro-4-nitrophenoxy)-pyrimidine

HRID 659012

反応式

HRID 659012 の反応式
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([OH:13])[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11].Cl[C:15]1[CH:20]=[CH:19][N:18]=[C:17]([S:21][CH3:22])[N:16]=1>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[O:13][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([S:21][CH3:22])[N:16]=1

参加物

5

反応物 3

HCID 102833-Chloro-4-nitrophenolHCID 24758Sodium hydrideHCID 971134-Chloro-2-methylthiopyrimidine

生成物 1

HCID 675239472-Methylsulfanyl-4-(3-chloro-4-nitrophenoxy)-pyrimidine収率 64.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

160 mg (6.34 mmol) 95% sodium hydride was given to a solution of 1.00 g (5.76 mmol) 3-chloro-4-nitrophenol in 15 ml DMF. Stirring was continued for 30 min. at room temperature. 925 mg (5.76 mmol) 4-chloro-2-methylsulfanyl-pyrimidine was added and the mixture heated to 80° C. for 16 h. The reaction mixture was evaporated, taken up with water and extracted with ethyl acetate. The organic phase was extracted with water, dried (sodium sulphate) and evaporated. The obtained material was dissolved in ethyl acetate and purified by chromatography over silica (ethyl acetate/n-heptane) to give 1.10 g (64%) 4-(3-chloro-4-nitro-phenoxy)-2-methylsulfanyl-pyrimidine.

後処理

  1. customThe reaction mixture was evaporated
  2. extractionextracted with ethyl acetate
  3. extractionThe organic phase was extracted with water
  4. dry with materialdried (sodium sulphate)
  5. customevaporated
  6. dissolutionThe obtained material was dissolved in ethyl acetate
  7. custompurified by chromatography over silica (ethyl acetate/n-heptane)

出典と根拠

ORDレコード
ord-33c7b7ddca184643b13bb176aaa90e9f
出典データセット
uspto-grants-2011_12
特許番号
US08080552B2

関連ノート

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