Triethylamine → 5-bromo-2-methoxy-N-methylbenzenesulfonamide

HRID 531438Notes

Reaction equation

HRID 531438 reaction equation
Cl.CN.[CH2:4]([N:6](CC)CC)C.[Br:11][C:12]1[CH:13]=[CH:14][C:15]([O:22][CH3:23])=[C:16]([S:18](Cl)(=[O:20])=[O:19])[CH:17]=1>C(Cl)Cl>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([O:22][CH3:23])=[C:16]([S:18]([NH:6][CH3:4])(=[O:20])=[O:19])[CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5200205-Bromo-2-methoxybenzene-1-sulfonyl chlorideHCID 6364545Methylamine hydrochloride

Product 1

HCID 84680955-bromo-2-methoxy-N-methylbenzenesulfonamideYield 81.63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred ice cold mixture of methylamine hydrochloride (231.1 mg, 3.5 mmol), triethylamine (1.26 mL, 8.755 mmol) in DCM was added a solution of 5-bromo-2-methoxybenzene-1-sulfonyl chloride (500 mg, 1.751 mmol) in DCM at 0° C. This was stirred at RT for three hours. This mixture was then poured on to ice cold water and extracted with DCM, dried over sodium sulfate and concentrated to get 400 mg (81.63% yield) of titled compound.

Workup

  1. additionThis mixture was then poured on to ice cold water
  2. extractionextracted with DCM
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a6df682d67b54c1591f8da11e2e9de8e
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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