HCID 23439403, compound → HCID 23439478, compound

HRID 2120376Notes

Reaction equation

HRID 2120376 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[C:6]([S:9][CH:10]([CH3:12])[CH3:11])[CH:5]=[CH:4][C:3]=1[N+:13]([O-])=O>O.CN(C=O)C.CCOC(C)=O.O.O.O.O.O.O.[Fe](Cl)(Cl)Cl.[Zn]>[Cl:1][C:2]1[C:7]([F:8])=[C:6]([S:9][CH:10]([CH3:12])[CH3:11])[CH:5]=[CH:4][C:3]=1[NH2:13]

Participants

7

Reactant 1

HCID 23439403HCID 23439403, compound

Product 1

HCID 23439478HCID 23439478, compoundYield 59.7%

Reagents, catalysts & solvents 5

HCID 23994ZincCatalystHCID 16211236Trichloroiron;hexahydrateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A solution of iron trichloride hexahydrate (32.7 g) in water (100 ml) was added to a mixture of 2-chloro-3-fluoro-4-(isopropylsulphanyl)nitrobenzene (Method 78; 10.07 g) and zinc dust (26.36 g) in DMF (100 ml). The mixture was heated to 100° C. for two hours and then allowed to cool to ambient temperature. It was then diluted with EtOAc (500 ml) filtered through diatomaceous earth, washed with brine (4×250 ml), dried over magnesium sulphate and volatile material was removed by evaporation to leave an oil. This was purified by chromatography on silica gel, eluted with 10% EtOAc in hexane to give the title compound (5.29 g) as a solid. NMR: 1.11 (d, 6H), 3.10 (septet, 1H), 5.92 (s, 2H), 6.57 (d, 1H), 7.11 (t, 1H); m/z 219 (M+).

Workup

  1. temperatureto cool to ambient temperature
  2. filtrationfiltered through diatomaceous earth
  3. washwashed with brine (4×250 ml)
  4. dry with materialdried over magnesium sulphate and volatile material
  5. customwas removed by evaporation
  6. customto leave an oil
  7. customThis was purified by chromatography on silica gel
  8. washeluted with 10% EtOAc in hexane

Sources & evidence

ORD record
ord-c47a69c1c0f044d6850e51c069d719ba
Source dataset
uspto-grants-2004_02
Patent number
US06689909B1

Reaction notes

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