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

HRID 659012

Reaction equation

HRID 659012 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-33c7b7ddca184643b13bb176aaa90e9f
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Linked notes

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