Pyridine → 4-bromo-N-methylbenzene-1-sulfonamide

HRID 594964Notes

Reaction equation

HRID 594964 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CN.[N:14]1C=CC=C[CH:15]=1>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:14][CH3:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6329MethylamineHCID 7396p-Bromobenzenesulfonyl chloride

Product 1

HCID 1012154-bromo-N-methylbenzene-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-bromo-N-methylbenzenesulfonamide was prepared by stirring a solution of 4-bromobenzenesulfonyl chloride (400 mg, 1.57 mmol), methylamine (0.78 mL, 2M solution in THF) and pyridine (1 mL) in dichloromethane (5 mL) was at rt for 16 h. The mixture was then diluted with dichloromethane and washed with H2O and then brine. The organic phase was collected, dried (MgSO4) and concentrated in vacuo to give 4-bromo-N-methylbenzenesulfonamide. 1H NMR (d6-DMSO) δ 10.12 (s, 1H0, 9.04 (s, 1H), 8.45 (d, 2H), 8.38 (s, 1H), 8.00 (d, 2H), 7.96 (s, 1H), 7.64 (s, 1H), 7.57 (s, 1H), 3.87 (s, 3H), 2.47 (s, 3H); LC-MS method B, (ES+) 385.0, RT=7.45 min.

Workup

  1. custom4-bromo-N-methylbenzenesulfonamide was prepared
  2. washwashed with H2O
  3. customThe organic phase was collected
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0a800e7b09e04bc6a00b681e7a5e63d1
Source dataset
uspto-grants-2016_01
Patent number
US09242987B2

Reaction notes

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