Hydrochloric Acid → HCID 86656449, compound

HRID 1028047Notes

Reaction equation

HRID 1028047 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([Cl:10])[N:7]=[CH:6][C:5]=1[N:11](S(C1C=CC([N+]([O-])=O)=CC=1)(=O)=O)[S:12]([C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)(=[O:14])=[O:13])(=[O:3])[CH3:2].[Li+].[OH-].Cl>C1COCC1.CO>[C:1]([C:4]1[CH:9]=[C:8]([Cl:10])[N:7]=[CH:6][C:5]=1[NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)(=[O:13])=[O:14])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86656448HCID 86656448, compound

Product 1

HCID 86656449HCID 86656449, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of N-(4-acetyl-6-chloropyridin-3-yl)-4-nitro-N-(4-nitrophenylsulfonyl)benzenesulfonamide (1.0 equiv.) in 2:1 THF/MeOH (0.05 M) was added 1 M LiOH (aq.) (3.1 equiv). The resulting purple solution was stirred at rt for 15 hours, at which time 1 M HCl (3.1 equiv) was added. The volatiles were removed in vacuo and ethyl acetate (700 mL) and H2O (200 mL) were added. Upon separating the organic was washed with NaHCO3(sat.) (200 mL), with NaCl(sat.) (200 mL), dried over MgSO4, filtered and concentrated. Purification by column chromatography (50% ethyl acetate/hexanes with 0.1% AcOH, Rf=0.6) yielded N-(4-acetyl-6-chloropyridin-3-yl)-4-nitrobenzenesulfonamide (84%). LCMS (m/z): 356.0 (MH+); LC Rt=3.81 min. 1H NMR (CDCl3): δ 8.89 (s, 1H), 8.32 (m, 2H), 8.06 (m, 2H), 7.62 (s, 1H), 2.60 (s, 3H).

Workup

  1. additionwas added
  2. customThe volatiles were removed in vacuo and ethyl acetate (700 mL) and H2O (200 mL)
  3. additionwere added
  4. customUpon separating the
  5. washorganic was washed with NaHCO3(sat.) (200 mL), with NaCl(sat.) (200 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by column chromatography (50% ethyl acetate/hexanes with 0.1% AcOH, Rf=0.6)

Sources & evidence

ORD record
ord-05dab64ac2d14f82b437c188d41fea1d
Source dataset
uspto-grants-2014_05
Patent number
US08735424B2

Reaction notes

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