Ethyl Bromide → 2-Acetamido-N-(thiophen-2-yl)-1-benzothiophene-3-carboxamide

HRID 434359

Reaction equation

HRID 434359 reaction equation
[Mg].C(Br)C.C([Mg]Br)C.[NH2:9][C:10]1[S:11][CH:12]=[CH:13][CH:14]=1.[C:15]([NH:18][C:19]1[S:23][C:22]2[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=2[C:20]=1[C:28]([O-])=[O:29])(=[O:17])[CH3:16]>O1CCCC1>[S:11]1[CH:12]=[CH:13][CH:14]=[C:10]1[NH:9][C:28]([C:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[S:23][C:19]=1[NH:18][C:15]([CH3:16])=[O:17])=[O:29]

Participants

7

Reactant 5

HCID 6332Ethyl BromideHCID 973732-AminothiopheneHCID 5462224Magnesium2×HCID 204936782-Acetamido-benzo[b]thiophen-3-carboxylateHCID 178418443HCID 178418443, compound

Product 1

HCID 131945492-Acetamido-N-(thiophen-2-yl)-1-benzothiophene-3-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

3 g of magnesium curlings and 30 ml of anhydrous tetrahydrofuran are initially introduced into a sulfonation flask and 13.5 g of ethyl bromide are added in order to prepare ethyl-magnesium bromide. After the magnesium has dissolved, 6.1 g of 2-aminothiophen, dissolved in 60 ml of absolute tetrahydrofuran, are added dropwise and the mixture is stirred for one hour at room temperature and then refluxed for a further 15 minutes. 8 g of . . . 2-acetamido-benzo[b]thiophen-3-carboxylate, dissolved in 100 ml of absolute tetrahydrofuran, are then added dropwise at room temperature. The mixture is then refluxed for 15 minutes and stirred for a further 15 minutes at room temperature, the reaction solution is evaporated in vacuo, dilute hydrochloric acid is added to the evaporation residue and the mixture is extracted twice with chloroform. The chloroform extracts are combined, dried over sodium sulfate and evaporated to dryness in vacuo. Crude N-(2-thienyl)-2-acetamino-benzo[b]thiophen-3-carboxamide is obtained and this can be used without further purification.

Workup

  1. additionare added dropwise
  2. temperaturerefluxed for a further 15 minutes
  3. additionare then added dropwise at room temperature
  4. temperatureThe mixture is then refluxed for 15 minutes
  5. stirringstirred for a further 15 minutes at room temperature
  6. customthe reaction solution is evaporated in vacuo, dilute hydrochloric acid
  7. additionis added to the evaporation residue
  8. extractionthe mixture is extracted twice with chloroform
  9. dry with materialdried over sodium sulfate
  10. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-6c50afda282540c8a7fd37d97b675dbf
Source dataset
uspto-grants-1983_08
Patent number
US04396621

Linked notes

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