Benzoyl chloride → N-[(5-Bromo-3-thienyl)methyl]-N-methylbenzamide

HRID 2426296Notes

Reaction equation

HRID 2426296 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:10][C:11]1[S:15][CH:14]=[C:13]([CH2:16][NH:17][CH3:18])[CH:12]=1.C(N(CC)CC)C>O1CCCC1>[Br:10][C:11]1[S:15][CH:14]=[C:13]([CH2:16][N:17]([CH3:18])[C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:12]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 43432000HCID 43432000, compound

Product 1

HCID 61394529N-[(5-Bromo-3-thienyl)methyl]-N-methylbenzamideYield 90.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.6 ml (13 mmol) of benzoyl chloride are added dropwise to a solution of 2.3 g (11 mmol) of (5-bromothiophen-3-ylmethyl)methylamine and 3 ml (22 mmol) of triethylamine in 30 ml of tetrahydrofuran. The reaction medium is stirred at room temperature for 1 hour, filtered, diluted with ethyl acetate and washed with water. The organic phase obtained is dried over sodium sulfate, filtered and evaporated to dryness. The residue obtained is purified by chromatography on a column of silica eluted with an 8/2 heptane/ethyl acetate mixture. 3.1 g (80%) of N-(5-bromothiophen-3-ylmethyl)-N-methylbenzamide are obtained.

Workup

  1. filtrationfiltered
  2. additiondiluted with ethyl acetate
  3. washwashed with water
  4. customThe organic phase obtained
  5. dry with materialis dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue obtained
  9. customis purified by chromatography on a column of silica
  10. washeluted with an 8/2 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-43cc8dac7a714307812e3d0994fe5aa6
Source dataset
uspto-grants-2011_06
Patent number
US07968560B2

Reaction notes

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