Triethylamine → 4-Bromothiophene-2-carboxamide

HRID 2206042Notes

Reaction equation

HRID 2206042 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:7]([OH:9])=O)[S:5][CH:6]=1.C([N:12](CC)CC)C.CCN=C=NCCCN(C)C.Cl>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([C:7]([NH2:12])=[O:9])[S:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6104094-Bromo-2-thiophenecarboxylic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 128360674-Bromothiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-bromothiophene-2-carboxylic acid (15 g), HOBt ammonium salt (16.5 g) and triethylamine (20.08 mL) in acetonitrile (250 mL) was added EDCI hydrochloride (16.87 g), and the mixture was stirred overnight. The reaction mixture was washed with saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (8.0 g).

Workup

  1. washThe reaction mixture was washed with saturated aqueous sodium bicarbonate solution and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0f1ba51f32a04372a29cf5d9aeac3bbb
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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