Thionyl Chloride → 3-[(4-Bromo-2,5-difluorobenzoyl)amino]thiophene-2-carboxamide

HRID 225459

Reaction equation

HRID 225459 reaction equation
[Br:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([F:12])[CH:3]=1.S(Cl)(Cl)=O.[NH2:17][C:18]1[CH:22]=[CH:21][S:20][C:19]=1[C:23]([NH2:25])=[O:24].C(N(CC)C(C)C)(C)C>C1COCC1>[Br:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([NH:17][C:18]2[CH:22]=[CH:21][S:20][C:19]=2[C:23]([NH2:25])=[O:24])=[O:8])=[C:4]([F:12])[CH:3]=1

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 5189933-Aminothiophene-2-carboxamideHCID 8228574-Bromo-2,5-difluorobenzoic acid

Product 1

HCID 577530493-[(4-Bromo-2,5-difluorobenzoyl)amino]thiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After stirring a mixture of 4-bromo-2,5-difluorobenzoic acid and thionyl chloride for one hour at 80° C., the solution was removed and an oily substance was obtained. A mixture of the obtained oily substance, 3-aminothiophene-2-carboxamide, N,N-diisopropylethylamine and THF was stirred for two hours under ice cooling to give 3-[(4-bromo-2,5-difluorobenzoyl)amino]thiophene-2-carboxamide.

Workup

  1. customthe solution was removed
  2. customan oily substance was obtained
  3. stirringwas stirred for two hours under ice cooling

Sources & evidence

ORD record
ord-ceaa1bcb15a74d6782e47e4c3384fc3c
Source dataset
uspto-grants-2009_07
Patent number
US07557112B2

Linked notes

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