2,4,6-Trimethylpyridine → N,N-Bis-(2-trifluoromethanesulfonyloxyethyl)-2-nitrobenzenesulfonamide

HRID 386520Notes

Reaction equation

HRID 386520 reaction equation
S([O:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])(C(F)(F)F)(=O)=O.[OH:16][CH2:17][CH2:18][N:19]([CH2:32][CH2:33]O)[S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N+:29]([O-:31])=[O:30])(=[O:22])=[O:21].N1C(C)=CC(C)=CC=1C>C(Cl)Cl.C(Cl)(Cl)Cl>[F:13][C:12]([F:15])([F:14])[S:9]([O:16][CH2:17][CH2:18][N:19]([CH2:32][CH2:33][O:8][S:9]([C:12]([F:13])([F:14])[F:15])(=[O:10])=[O:11])[S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N+:29]([O-:31])=[O:30])(=[O:22])=[O:21])(=[O:10])=[O:8]

Participants

6

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 60723400N,N-Bis-(2-hydroxy-ethyl)-2-nitrobenzenesulfonamide

Product 1

HCID 86601384N,N-Bis-(2-trifluoromethanesulfonyloxyethyl)-2-nitrobenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triflic anhydride (13.6 g, 48.3 mmol) was added dropwise with stirring to a 0° C. solution of N,N-bis-(2-hydroxyethyl)-2-nitrobenzenesulfonamide (7.00 g, 24.1 mmol) from Example 16A and 2,4,6-collidine (5.85 g, 48.3 mmol) in anhydrous methylene chloride (50 mL) (J. A. Kozlowski, et al., Bioorg. Med. Chem. Lett. 12: 791-794, 2002). Reaction stirred two hours at 0° C. and then overnight at room temperature. Reaction diluted with chloroform, washed with saturated NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by normal phase HPLC on a Biotage pre-packed silica gel column eluting with 3:1 hexane:ethyl acetate to afford the title compound. MS (ESI) m/z 555 (M+H)+.

Workup

  1. customReaction
  2. customovernight
  3. customat room temperature
  4. customReaction
  5. washwashed with saturated NaHCO3 and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by normal phase HPLC on a Biotage pre-packed silica gel column
  10. washeluting with 3:1 hexane

Sources & evidence

ORD record
ord-ba5630cb4eb44af1984db333bec36d53
Source dataset
uspto-grants-2013_02
Patent number
US08372841B2

Reaction notes

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