Hydrochloric Acid → N-(3-chloro-4-hydroxynaphthalen-1-yl)thiophene-2-sulfonamide

HRID 1258373Notes

Reaction equation

HRID 1258373 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12][S:13]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)(=[O:15])=[O:14])=[CH:4][CH:3]=1.OO.[ClH:23]>CO>[Cl:23][C:3]1[CH:4]=[C:5]([NH:12][S:13]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)(=[O:15])=[O:14])[C:6]2[C:11]([C:2]=1[OH:1])=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 784Hydrogen Peroxide2×HCID 697391N-(4-hydroxynaphthalen-1-yl)thiophene-2-sulfonamide

Product 1

HCID 3718048N-(3-chloro-4-hydroxynaphthalen-1-yl)thiophene-2-sulfonamideYield 22.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.987 g N-(4-hydroxynaphthalen-1-yl)thiophene-2-sulfonamide (3) was suspended in 10 ml methanol, to which was added 3 ml hydrogen peroxide solution (35%). The mixture was stirred at r.t. for 2 h. Additional 3 ml hydrogen peroxide solution was added followed by 1 ml HCl solution (4 M in dioxane). The reaction was continued for another 2 h. The organic solvent was removed via rotavap and the residue was redissolved in ethyl acetate (100 ml). Washed with water (20 ml×3) and brine (20 ml×2), the organic phase was dried over Mg2SO4. The organic phase was filtered and concentrated. The crude product was separated via flash chromatography (Hex/EtOAc) affording 244 mg (22.2%) brown solid, m.p.: 113-115° C.

Workup

  1. waitThe reaction was continued for another 2 h
  2. customThe organic solvent was removed via rotavap
  3. dissolutionthe residue was redissolved in ethyl acetate (100 ml)
  4. washWashed with water (20 ml×3) and brine (20 ml×2)
  5. dry with materialthe organic phase was dried over Mg2SO4
  6. filtrationThe organic phase was filtered
  7. concentrationconcentrated
  8. customThe crude product was separated via flash chromatography (Hex/EtOAc)

Sources & evidence

ORD record
ord-d24339464a494b45a7f01ba07f3bb521
Source dataset
uspto-grants-2013_06
Patent number
US08466157B2

Reaction notes

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