Pyridine → HCID 668999, compound

HRID 1049035Notes

Reaction equation

HRID 1049035 reaction equation
[CH2:1]([NH2:5])[CH:2]([CH3:4])[CH3:3].N1C=CC=CC=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>C(Cl)Cl>[F:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:5][CH2:1][CH:2]([CH3:4])[CH3:3])(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6558IsobutylamineHCID 95884-Fluorobenzenesulfonyl chloride

Product 1

HCID 668999HCID 668999, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of isobutylamine (6.64 mL, 66.8 mmol) and pyridine (6.24 mL, 77.1 mmol) in DCM (100 mL) was treated with 4-fluorobenzene sulfonyl chloride (10.0 g, 51.4 mmol) and stirred at room temperature for 18 hours. The mixture was diluted with DCM, washed with 1 N aqueous HCl, saturated aqueous NaHCO3, water and brine, dried over Na2SO4 and concentrated under vacuum. Trituration with pentane gave 4-fluoro-N-isobutyl-benzenesulfonamide (10.48 g, 88%) as a pale yellow solid. 1H NMR (400 MHz, DMSO) δ 7.88-7.81 (m, 2H), 7.63 (t, J=6.1 Hz, 1H), 7.47-7.39 (m, 2H), 2.54 (t, J=6.5 Hz, 2H), 1.67-1.55 (m, 1H), 0.80 (d, J=6.7 Hz, 6H). LCMS (m/z, Method B) ES+ 232.0 [M+1]+.

Workup

  1. washwashed with 1 N aqueous HCl, saturated aqueous NaHCO3, water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7510f2da7f8b420fabcbfbe9a4164255
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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