Trifluoroacetic acid → 3-Amino-5-bromothiophene-2-carboxamide

HRID 11425Notes

Reaction equation

HRID 11425 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([NH2:9])=[O:8])=[C:4]([NH:10]C(OC(C)(C)C)=O)[CH:3]=1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl>[NH2:10][C:4]1[CH:3]=[C:2]([Br:1])[S:6][C:5]=1[C:7]([NH2:9])=[O:8]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 21975856tert-Butyl (5-bromo-2-carbamoylthiophen-3-yl)carbamate

Product 1

HCID 219758623-Amino-5-bromothiophene-2-carboxamideYield 97.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Bromo-3-(t-butyloxycarbonyl)aminothiophene-2-carboxamide (0.76 g) was stirred in dichloromethane (30 ml). Trifluoroacetic acid (51 ml) was added, the solution was stirred at room temperature for 1 h, poured into saturated aqueous sodium hydrogen carbonate solution (200 ml) and extracted with dichloromethane (3×100 ml). The combined extracts were washed with brine (150 ml), dried (magnesium sulphate), filtered and evaporated to give a yellow solid (0.511 g).

Workup

  1. extractionextracted with dichloromethane (3×100 ml)
  2. washThe combined extracts were washed with brine (150 ml)
  3. dry with materialdried (magnesium sulphate)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-a3b9c32ae59b4f06a3e70b55003233e4
Source dataset
uspto-grants-2006_08
Patent number
US07098240B2

Reaction notes

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