Nitromethane → 3-[5-(2-Methylsulfanyl-pyrimidin-4-yl)-thiophen-2-yl]-4-nitro-butyric acid methyl ester

HRID 1434923Notes

Reaction equation

HRID 1434923 reaction equation
[CH3:1][O:2][C:3](=[O:19])/[CH:4]=[CH:5]/[C:6]1[S:7][C:8]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=2)=[CH:9][CH:10]=1.[N+:20]([CH3:23])([O-:22])=[O:21]>CCOC(C)=O>[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH:5]([C:6]1[S:7][C:8]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=2)=[CH:9][CH:10]=1)[CH2:23][N+:20]([O-:22])=[O:21]

Participants

4

Reactant 2

HCID 6375NitromethaneHCID 57936328(E)-3-[5-(2-Methylsulfanyl-pyrimidin-4-yl)-thiophen-2-yl]-acrylic acid methyl ester

Product 1

HCID 579361643-[5-(2-Methylsulfanyl-pyrimidin-4-yl)-thiophen-2-yl]-4-nitro-butyric acid methyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (E)-3-[5-(2-methylsulfanyl-pyrimidin-4-yl)-thiophen-2-yl]-acrylic acid methyl ester (200 mg, 0.684 mmol), nitromethane (3 ml) and Triton B (0.3 ml) was heated to 80° C. for 4 hours. After cooling, the mixture was diluted with EtOAc and washed with saturated ammonium chloride solution, water and brine. Drying over sodium sulfate and evaporation gave a red-brown oil. Yield: 100 mg (41%)

Workup

  1. temperatureAfter cooling
  2. washwashed with saturated ammonium chloride solution, water and brine
  3. dry with materialDrying over sodium sulfate and evaporation
  4. customgave a red-brown oil

Sources & evidence

ORD record
ord-9f01fab818324c948d7f6852bda59d57
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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