Water → 5-Bromo-N-(tert-butyl)pyridine-2-sulfonamide

HRID 1772661Notes

Reaction equation

HRID 1772661 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8](Cl)(=[O:10])=[O:9])=[N:6][CH:7]=1.[C:12]([NH2:16])([CH3:15])([CH3:14])[CH3:13].O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:16][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])=[O:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6385Tert-ButylamineHCID 445580975-Bromopyridine-2-sulfonyl chloride

Product 1

HCID 711166495-Bromo-N-(tert-butyl)pyridine-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-bromopyridine-2-sulfonyl chloride (2.7 g, 10 mmol) in DCM (100 mL) was cooled to 0° C. and treated with tert-BuNH2 (5.5 mL, 52 mmol). The resulting mixture was stirred at rt for 48 h. Water (50 mL) was added and the DCM layer were separated, dried and concentrated to obtain compound 32a. 1H-NMR (400 MHz, CDCl3) δ (ppm): 8.75 (d, J=2.3 Hz, 1H), 8.03 (dd, J=8.2, 2.3 Hz, 1H), 7.90-7.94 (m, 1H), 5.02-5.07 (m, 1H), 1.23 (s, 9H).

Workup

  1. customthe DCM layer were separated
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ecd019b54a7644189cf319967949951e
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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