1-Propanesulfonyl chloride → HCID 69810002, compound

HRID 535721Notes

Reaction equation

HRID 535721 reaction equation
[Br:1][C:2]1[C:3]([F:10])=[C:4]([CH:6]=[C:7]([Cl:9])[CH:8]=1)[NH2:5].[CH2:11]([S:14](Cl)(=[O:16])=[O:15])[CH2:12][CH3:13]>N1C=CC=CC=1>[Br:1][C:2]1[C:3]([F:10])=[C:4]([NH:5][S:14]([CH2:11][CH2:12][CH3:13])(=[O:16])=[O:15])[CH:6]=[C:7]([Cl:9])[CH:8]=1

Participants

4

Reactant 2

HCID 662791-Propanesulfonyl chlorideHCID 510342253-Bromo-5-chloro-2-fluorobenzenamine

Product 1

HCID 69810002HCID 69810002, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-bromo-5-chloro-2-fluoroaniline (SM-5, step 3, 0.52 g, 2.3 mmol) in pyridine (2.5 mL) cooled in an ice water bath was added propane-1-sulfonyl chloride (0.3 mL, 2.8 mmol). After 4 hours the solution was concentrated and partitioned between EtOAc (75 mL) and aqueous 0.1 M HCl solution (30 mL). The layers were separated and the organic phase was then washed with brine, dried (Na2SO4) and concentrated to give 778 mg of N-(3-bromo-5-chloro-2-fluorophenyl)propane-1-sulfonamide as a yellow solid which was carried forward without further purification: LCMS (m/z) not observed, tR=0.95 minute.

Workup

  1. concentrationAfter 4 hours the solution was concentrated
  2. custompartitioned between EtOAc (75 mL) and aqueous 0.1 M HCl solution (30 mL)
  3. customThe layers were separated
  4. washthe organic phase was then washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-37543bf2fd7e4b0489872bb607b8883c
Source dataset
uspto-grants-2014_10
Patent number
US08859548B2

Reaction notes

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