Tert-Butylamine → 5-Bromo-N-tert-butylpyridine-3-sulfonamide

HRID 2036779Notes

Reaction equation

HRID 2036779 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[N:6][CH:7]=1.[C:12]([NH2:16])([CH3:15])([CH3:14])[CH3:13]>C1COCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([S:8]([NH:16][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])=[O:9])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 6385Tert-ButylamineHCID 203244745-Bromopyridine-3-sulfonyl chloride

Product 1

HCID 617949515-Bromo-N-tert-butylpyridine-3-sulfonamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
2.5 °C

Procedure

Crude 5-bromopyridine-3-sulfonyl chloride from step 1 above was dissolved in THF (14 L, 8 vol) and then transferred to a 20 L RB flask equipped with mechanical stirrer under inert atmosphere. The solution was cooled to 0-5° C. and tert-butyl amine (1.95 Kg, 26.66 moles) was added at 0-5° C. Upon completion of addition, the reaction mixture was warmed to ambient temperature where it stirred for 2 h. At the conclusion of this period, the reaction progress was monitored by HPLC, which indicated that the reaction was complete. The solvent was evaporated under vacuum to give a thick residue. The residue was dissolved in ethyl acetate (18 L, 12 vol). The organic layer was separated, washed with water (9 L, 5 vol) and then concentrated under vacuum to yield a residue. Hexanes (9 L, 5 vol) were added to the residue and the product precipitated out and was collected by filtration to yield a free flowing yellow solid (1.5 Kg, 54.28% overall yield). 1H NMR (DMSO-D6, 400 MHz, δ ppm); 8.99 (d, J=2 Hz, 1H), 8.81 (d, J=2 Hz, 1H), 8.29 (t, J=2 Hz, 1H). [M++1]=293.

Workup

  1. customtransferred to a 20 L RB flask
  2. customequipped with mechanical stirrer under inert atmosphere
  3. additionUpon completion of addition
  4. temperaturethe reaction mixture was warmed to ambient temperature where it
  5. customThe solvent was evaporated under vacuum
  6. customto give a thick residue
  7. customThe organic layer was separated
  8. washwashed with water (9 L, 5 vol)
  9. concentrationconcentrated under vacuum
  10. customto yield a residue
  11. customthe product precipitated out
  12. filtrationwas collected by filtration
  13. customto yield
  14. customsolid (1.5 Kg, 54.28% overall yield)

Sources & evidence

ORD record
ord-502214a0452843ea98977473293b5202
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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