Thiophene → 2-Chloro-5-(thiophene-2-carbonyl)-benzenesulfonamide

HRID 1810191Notes

Reaction equation

HRID 1810191 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.C([Li])CCC.[Cl:11][C:12]1[CH:23]=[CH:22][C:15]([C:16](N(OC)C)=[O:17])=[CH:14][C:13]=1[S:24](=[O:27])(=[O:26])[NH2:25]>O1CCCC1>[Cl:11][C:12]1[CH:23]=[CH:22][C:15]([C:16]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[O:17])=[CH:14][C:13]=1[S:24]([NH2:25])(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 8030ThiopheneHCID 581073994-chloro-N-methoxy-N-methyl-3-sulfamoyl-benzamideHCID 178418339Butyllithium

Product 1

HCID 581074962-Chloro-5-(thiophene-2-carbonyl)-benzenesulfonamideYield 18.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of thiophene (0.27 g, 3.20 mmol) dissolved in tetrahydrofuran (10 mL) at −78° C. under nitrogen is dropwisely added 1.6 M of n-butyllithium (2 mL, 3.40 mmol). The reaction mixture is stirred at −78° C. for 1 h then a solution 4-chloro-N-methoxy-N-methyl-3-sulfamoyl-benzamide (0.3 g, 1.08 mmol) in tetrahydrofuran (2 mL) is added slowly and the reaction mixture is allowed to warm to room temperature and stirred for 1 h. The reaction is quenched with saturated ammonium chloride and extracted with ethyl acetate three times. The combined organic extracts are washed with a saturated sodium chloride solution, dried with magnesium sulfate, and concentrated in vacuo. Purification by silica gel chromatography (50% ethyl acetate-hexane) provides 0.059 g (18%) of the title compound as a yellow solid. 1H NMR (DMSO): δ 8.33 (d, J=2 Hz, 1H), 8.15 (dd, J=4, 1 Hz, 1H), 8.05 (dd, J=8, 4 Hz, 1H), 7.85 (m, 4H), 7.35 (m, 1H). Analytics calculated for C11H8ClO3S2: C, 43.78; H, 2.67; N, 4.64. Found: C, 43.70; H, 2.61; N, 4.61. MS (m/z): 300.0 (M−1).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 1 h
  3. customThe reaction is quenched with saturated ammonium chloride
  4. extractionextracted with ethyl acetate three times
  5. washThe combined organic extracts are washed with a saturated sodium chloride solution
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customPurification by silica gel chromatography (50% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-7261e7ae8b2140d0b9969682a940bdb2
Source dataset
uspto-grants-2013_01
Patent number
US08362063B2

Reaction notes

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