Ammonia → 5-Bromothiophene-2-carboxamide

HRID 1921761Notes

Reaction equation

HRID 1921761 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][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[S:6][C:5]([C:7]([NH2:12])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 3491155-Bromothiophene-2-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 6057225-Bromothiophene-2-carboxamideYield 84.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-bromo-thiophene-2-carboxylic acid (4.51 g, 21.78 mmol), 3-hydroxybenzotriazole hydrate (3.24 g, 23.96 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)-carbodiimide (4.6 g, 23.96 mmol) in DMF (70 mL) is stirred at room temperature for 2 hours. The reaction mixture is then cooled to 0° C. and aq. 35% NH3 (2.2 mL) is added. The mixture is stirred at room temperature overnight. The solvent is removed in vacuo and the residue dissolved in EtOAc, washed with 1N NaHCO3, and brine. The organic layers are combined, dried over MgSO4, filtered and concentrated to afford the title compound (3.78 g, 84%). HPLC (254 nm): Rt 2.46 min (96.5%).

Workup

  1. customThe solvent is removed in vacuo
  2. dissolutionthe residue dissolved in EtOAc
  3. washwashed with 1N NaHCO3, and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2eff163a45034f5fb0432121c93c86dd
Source dataset
uspto-grants-2012_05
Patent number
US08173656B2

Reaction notes

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