Ammonia → 4-Bromothiophene-2-carboxamide

HRID 1921806Notes

Reaction equation

HRID 1921806 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.N>CN(C=O)C.O>[Br:1][C:2]1[CH:16]=[C:17]([C:18]([NH2:19])=[O:23])[S:4][CH:3]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 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 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In the same way as described for Compound 179, step 2, using 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), 1-hydroxybenzotriazole hydrate (1.44 g, 10.63 mmol) and aq. NH3 (1 ml, 17.3 mmol) in DMF (20 ml). Water is added to the reaction mixture and the resultant precipitate is collected by filtration and washed with 1M NaOH, H2O and petrol. The title compound is isolated as a white solid (1.56 g, 78%).

Workup

  1. filtrationthe resultant precipitate is collected by filtration
  2. washwashed with 1M NaOH, H2O and petrol

Sources & evidence

ORD record
ord-2a96515b94e5431bb1d537db82176481
Source dataset
uspto-grants-2012_05
Patent number
US08173656B2

Reaction notes

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