Triethylamine → 3-bromo-N-methylbenzene-1-sulfonamide

HRID 2042224Notes

Reaction equation

HRID 2042224 reaction equation
Cl.CN.[CH2:4]([N:6](CC)CC)C.[Br:11][C:12]1[CH:13]=[C:14]([S:18](Cl)(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=1>ClCCl>[Br:11][C:12]1[CH:13]=[C:14]([S:18]([NH:6][CH3:4])(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 17943m-Bromobenzenesulphonyl chlorideHCID 6364545Methylamine hydrochloride

Product 1

HCID 72132653-bromo-N-methylbenzene-1-sulfonamideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methylamine hydrochloride (1057 mg, 15.65 mmol) and triethylamine (3.3 mL, 23.48 mmol) were dissolved in dichloromethane (20 mL) and then 3-bromobenzene-1-sulfonyl chloride (4.0 g, 15.65 mmol) was slowly added. The reaction mixture was stirred at room temperature for 2 hours, diluted with dichloromethane, and washed with brine. The organic layer was dried with magnesium sulfate, filtered with celite, and then concentrated. The resultant target compound (3.5 g, 90% yield) was used in the following reaction without purification.

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. filtrationfiltered with celite
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-61980d8ba9bb430d919dada04c5d25b4
Source dataset
uspto-grants-2013_11
Patent number
US08586580B2

Reaction notes

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