HCID 67551310, compound → HCID 69844672, compound

HRID 1860252Notes

Reaction equation

HRID 1860252 reaction equation
[C:1]([C:4]1[S:8][C:7]([N+:9]([O-])=O)=[C:6]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]=1)(=[O:3])[NH2:2]>O1CCOCC1.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+2]>[NH2:9][C:7]1[S:8][C:4]([C:1](=[O:3])[NH2:2])=[CH:5][C:6]=1[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 1

HCID 67551310HCID 67551310, compound

Product 1

HCID 69844672HCID 69844672, compoundYield 95.9%

Reagents, catalysts & solvents 2

HCID 62662Ferrous sulfate heptahydrateCatalystHCID 312751,4-DioxaneSolvent

Procedure

Ethyl 5-carbamoyl-2-nitrothiophene-3-acetate (600 mg, 2.33 mmol) was dissolved in aqueous dioxan (7 ml, 4:1 dioxan/water) and treated with reduced iron powder (1.55 g, 27.77 mmol) and iron sulfate heptahydrate (200 mg, 0.68 mmol). The reaction mixture was refluxed for 1 hour then filtered through celite filter-aid and washed through with ethyl acetate. The organic phase was washed with saturated sodium aqueous hydrogen carbonate and saturated aqueous sodium chloride. The organic phase was dried over magnesium sulfate and evaporated to a red/black viscous oil and then chromatographed on silica gel using hexane/ethyl acetate (1:2) as eluent to give 510 mg of ethyl 2-amino-5-carbamoylthiophene-3-acetate. MS(ES): m/e 229 [M+H].

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. filtrationthen filtered through celite
  3. filtrationfilter-aid
  4. washwashed through with ethyl acetate
  5. washThe organic phase was washed with saturated sodium aqueous hydrogen carbonate and saturated aqueous sodium chloride
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. customevaporated to a red/black viscous oil
  8. customchromatographed on silica gel

Sources & evidence

ORD record
ord-c00322cac04e47d09ccc31fc526d3fa5
Source dataset
uspto-grants-2003_03
Patent number
US06528653B2

Reaction notes

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