Tert-Butylamine → N-tert-butyl-6-chloropyridine-3-sulfonamide

HRID 45231Notes

Reaction equation

HRID 45231 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[Cl:6][C:7]1[N:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1>C(Cl)Cl>[C:1]([NH:5][S:13]([C:10]1[CH:11]=[N:12][C:7]([Cl:6])=[CH:8][CH:9]=1)(=[O:15])=[O:14])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 27927922-Chloro-5-pyridinesulfonyl chloride

Product 1

HCID 4729821N-tert-butyl-6-chloropyridine-3-sulfonamideYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of 17.3 mL (165 mmol) of tert-butylamine and 69 mL (495 mmol) of TEA in 330 mL of DCM are added portionwise, at 0° C., 35 g (165 mmol) of 6-chloropyridine-3-sulfonyl chloride. After stirring for 2 hours at 0° C., the reaction medium is taken up in 600 mL of DCM, washed with water (1 L), saturated NaHCO3 solution (1 L) and brine (1 L), dried over Na2SO4, filtered and concentrated under reduced pressure. 32.4 g of N-tertbutyl-6-chloropyridine-3-sulfonamide are obtained in the form of a white solid.

Workup

  1. additionare added portionwise, at 0° C.
  2. washwashed with water (1 L), saturated NaHCO3 solution (1 L) and brine (1 L)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8127a537d4e242ff81ca2df85f83c037
Source dataset
uspto-grants-2013_09
Patent number
US08541455B2

Reaction notes

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