Bromine → 2-Acetamido-5-bromothiophene-3-carboxamide

HRID 2223363Notes

Reaction equation

HRID 2223363 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[CH:8][C:9]=1[C:10]([NH2:12])=[O:11])(=[O:3])[CH3:2].C([O-])(=O)C.[Na+].[Br:18]Br>>[C:1]([NH:4][C:5]1[S:6][C:7]([Br:18])=[CH:8][C:9]=1[C:10]([NH2:12])=[O:11])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 6852048HCID 6852048, compound

Product 1

HCID 693131752-Acetamido-5-bromothiophene-3-carboxamideYield 13.9%

Procedure

2-Acetylamino-thiophene-3-carboxylic acid amide (3.89 g, 27.4 mmol) was suspended in the aqueous solution of sodium acetate (2.47 g, 30.1 mmol)(136 mL). Bromine (1.4 mL, 27.4 mmol) was added dropwise to the solution. The resulting solution was stirred under nitrogen overnight. Once the LC-MS showed no remaining starting materials, the reaction mixture was then filtered and washed with water (50 mL). The filtrate was then purified utilizing a Gilson preparative. HPLC to give the above titled compound as a brown solid (1 g, 13.8%). LC-MS [M+H]+ m/z 263.

Workup

  1. filtrationthe reaction mixture was then filtered
  2. washwashed with water (50 mL)
  3. customThe filtrate was then purified

Sources & evidence

ORD record
ord-1fff3a9d156b4f8ab8cdb11a50f2b6a9
Source dataset
uspto-grants-2008_05
Patent number
US07375131B2

Reaction notes

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