Pyridine → HCID 65482177, compound

HRID 1049052Notes

Reaction equation

HRID 1049052 reaction equation
[CH2:1]([NH2:5])[CH:2]([CH3:4])[CH3:3].N1C=CC=CC=1.[Br:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>C(Cl)Cl>[Br:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([S:20]([NH:5][CH2:1][CH:2]([CH3:4])[CH3:3])(=[O:22])=[O:21])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6558IsobutylamineHCID 27344094-(Bromomethyl)benzenesulfonyl chloride

Product 1

HCID 65482177HCID 65482177, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of isobutylamine (1.10 mL, 11.14 mmol) and pyridine (600 μL, 7.42 mmol) in DCM (60 mL) was treated with 4-(bromomethyl)benzene sulfonyl chloride (2.00 g, 7.42 mmol) and stirred at room temperature for 1.5 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. Purification by silica gel column chromatography (0-50% EtOAc in cyclohexane) gave 4-bromomethyl-N-isobutyl-benzenesulfonamide (1.08 g, 48%). 1H NMR (300 MHz, CDCl3) δ 7.83 (d, J=8.1 Hz, 2H), 7.53 (d, J=8.1 Hz, 2H), 4.50 (s, 2H), 4.43 (t, J=6.4 Hz, 1H), 2.78 (t, J=6.6 Hz, 2H), 1.81-1.65 (m, 1H), 0.88 (d, J=6.7 Hz, 6H). LCMS (m/z, Method A) ES+ 308.0 [M+Na]+.

Workup

  1. washwashed with 1 N aqueous HCl, saturated aqueous NaHCO3, water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. customPurification by silica gel column chromatography (0-50% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-1f0752b13b1d49e1afd6e8c12eacadb5
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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