Ammonia → 4-Bromothiophene-2-carboxamide

HRID 1924956Notes

Reaction equation

HRID 1924956 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-08bcc8fd30c948749816798297ce2dbb
Source dataset
uspto-grants-2012_05
Patent number
US08178530B2

Reaction notes

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