Triethylamine → N-(4-bromo-3-chlorophenyl)methanesulfonamide

HRID 1405086Notes

Reaction equation

HRID 1405086 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[Cl:9].C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C1COCC1>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][S:18]([CH3:17])(=[O:20])=[O:19])=[CH:4][C:3]=1[Cl:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 888884-Bromo-3-chloroaniline

Product 1

HCID 22193858N-(4-bromo-3-chlorophenyl)methanesulfonamideYield 21.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Intermediate 62A (0.843 g, 4.08 mmol) in THF (20.41 mL) was added triethylamine (5.69 mL, 40.8 mmol) followed by methanesulfonyl chloride (0.414 mL, 5.31 mmol). The reaction mixture was allowed to stir at room temperature for 3 days, then quenched with a saturated aqueous solution of NaHCO3 and diluted with EtOAc. The layers were separated and the aqueous phase was extracted with EtOAc (2×). The organic phases were combined, dried over Na2SO4, filtered, and concentrated to afford the title compound (245 mg, 0.861 mmol, 21.09% yield) as a white solid. HPLC Ret timej: 1.32 min. MS (ES): m/z=284.2 [M+H]−. Intermediate 62 was used in the synthesis of Example 212.

Workup

  1. customquenched with a saturated aqueous solution of NaHCO3
  2. additiondiluted with EtOAc
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with EtOAc (2×)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2c2e4693017549848056480b352c7ce9
Source dataset
uspto-grants-2014_12
Patent number
US08916553B2

Reaction notes

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