Citric Acid → HCID 178449961, compound

HRID 2170162Notes

Reaction equation

HRID 2170162 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:8])=[N:6][CH:7]=1.Cl[S:10]([OH:13])(=O)=[O:11].[C:14]([NH2:18])([CH3:17])([CH3:16])[CH3:15].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.O>[Br:1][C:2]1[CH:3]=[C:4]([S:10]([NH:18][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:13])=[O:11])[C:5]([OH:8])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 6385Tert-ButylamineHCID 24638Chlorosulfonic acidHCID 178515818HCID 178515818, compound

Product 1

HCID 178449961HCID 178449961, compoundYield 14.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-bromopyridin-2-ol (1.00 g, 5.75 mmol) in chlorosulfonic acid (15.0 mL, 224 mmol) was heated to 150° C. for 14 h. The reaction mixture was added dropwise to tert-butyl amine (25 mL) in THF (25 mL) at 0° C. and was evaporated under reduced pressure to give a brown residue. The residue was dissolved in water (100 mL) and acidified with saturated citric acid solution (pH=6) and extracted with ethyl acetate (2×100 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to a residue which was purified by column chromatography using CombiFlash (REDISEP®, silica gel, 24 g, 60% EtOAc/hexanes) to obtain 5-bromo-N-(tert-butyl)-2-hydroxypyridine-3-sulfonamide (0.260 g, 14.6%). LCMS Condition B-24: retention time 1.10 min, [M+2]=309.0.

Workup

  1. customwas evaporated under reduced pressure
  2. customto give a brown residue
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure to a residue which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-e575ce1b730c4ee2bd445e4addd081af
Source dataset
uspto-grants-2015_06
Patent number
US09050345B2

Reaction notes

Loading…