Water → 4-Bromothiophene-2-carboxamide

HRID 605900Notes

Reaction equation

HRID 605900 reaction equation
[Br:1][C:2]1C=C[S:4][C:3]=1C(O)=O.Cl.C(N=C=N[CH2:16][CH2:17][CH2:18][N:19](C)C)C.O.[OH:23]N1C2C=CC=CC=2N=N1.O>CN(C=O)C>[Br:1][C:2]1[CH:16]=[C:17]([C:18]([NH2:19])=[O:23])[S:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27396883-Bromothiophene-2-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 128360674-Bromothiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4 bromo-thiophene-2-carboxylic acid (2.0 g, 9.66 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (2.04 g, 10.63 mmol) and 1-hydroxybenzotriazole hydrate (1.44 g, 10.63 mmol) in DMF (20 mL) is stirred at room temperature for 2 hours. The reaction mixture is then cooled to 0° C. and aq. NE3 (1 mL, 17.3 mmol) is added. The mixture is stirred at room temperature for an additional 5 hours, then water is added to the reaction mixture and the resultant precipitate is collected by filtration and washed with 1M NaOH, H2O and petroleum ether. The title compound is isolated as a white solid (1.56 g, 78%).

Workup

  1. addition(1 mL, 17.3 mmol) is added
  2. filtrationthe resultant precipitate is collected by filtration
  3. washwashed with 1M NaOH, H2O and petroleum ether

Sources & evidence

ORD record
ord-fd45deae34d4459aa8d0fec74c36bbb3
Source dataset
uspto-grants-2011_03
Patent number
US07915256B2

Reaction notes

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