Ammonia → 5-Bromofuran-3-carboxamide

HRID 1921809Notes

Reaction equation

HRID 1921809 reaction equation
[Br:1][C:2]1[O:6][CH:5]=[C:4]([C:7]([OH:9])=O)[CH:3]=1.O.O[N:12]1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.N>CN(C=O)C>[Br:1][C:2]1[O:6][CH:5]=[C:4]([C:7]([NH2:12])=[O:9])[CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 133335605-Bromofuran-3-carboxylic acid

Product 1

HCID 108214945-Bromofuran-3-carboxamideYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-bromo-furan-3-carboxylic acid (0.364 g, 1.92 mmol), 3-hydroxybenzotriazole hydrate (0.28 g, 2.11 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (0.40 g, 2.11 mmol) in DMF (11 mL) is stirred at room temperature for 2 hours. The reaction mixture is then cooled to 0° C. and aq. NH3 (0.22 mL) is added. The mixture is stirred at room temperature for an additional 5 hours, then the solvent is removed in vacuo and the residue dissolved in EtOAc, washed with 1N NaOH, and 1N HCl. The organic layers are combined, dried over MgSO4 and concentrated to afford the title compound (0.288 g, 79%). HPLC (254 nm): Rt 2.17 min (85.3%).

Workup

  1. customthe solvent is removed in vacuo
  2. dissolutionthe residue dissolved in EtOAc
  3. washwashed with 1N NaOH, and 1N HCl
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e24461adca0249f5aed30aee20eec9f9
Source dataset
uspto-grants-2012_05
Patent number
US08173656B2

Reaction notes

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