Benzenesulfonyl chloride → N-(2-(3-Chlorophenyl)pent-4-enyl)-N-methylbenzenesulfonamide

HRID 1737446Notes

Reaction equation

HRID 1737446 reaction equation
[CH3:1][NH:2][CH2:3][CH:4]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=1)[CH2:5][CH:6]=[CH2:7].C(=O)(O)[O-].[Na+].[C:20]1([S:26](Cl)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(OCC)(=O)C.O>[Cl:14][C:10]1[CH:9]=[C:8]([CH:4]([CH2:5][CH:6]=[CH2:7])[CH2:3][N:2]([CH3:1])[S:26]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:28])=[O:27])[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 23285277N-Methyl-(2-(3-chlorophenyl)pent-4-enyl)amine

Product 1

HCID 23285190N-(2-(3-Chlorophenyl)pent-4-enyl)-N-methylbenzenesulfonamideYield 61.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Methyl-(2-(3-chlorophenyl)pent-4-enyl)amine (202 mg, 1.03 mmol) was dissolved in 10 mL of ethyl acetate. A solution of sodium bicarbonate (766 mg, 10.3 mmol) in water (10 mL) was added followed by benzenesulfonyl chloride (363 mg, 4.06 mmol), and the heterogeneous mixture was stirred overnight at room temperature. The mixture was extracted with 5 mL of ethyl acetate followed by an additional 2×15 mL of ethyl acetate. The combined organic layers were dried over sodium sulfate, decanted, and evaporated. The residue was purified by flash column chromatography on silica gel, eluting with 10-20% ethyl ether in hexane to give 223 mg the title compound. 1NMR (400 MHz, CDCl3): δ 7.72 (d, 2H, J=8 Hz), 7.58 (tt, 1H, J=8, 1 Hz), 7.50 (t, 2H, J=8 Hz), 7.24 (d, 1H, J=8 Hz), 7.20 (dt, 1H, J=8, 1 Hz), 7.14 (t, 1H, J=1 Hz), 7.10 (dt, 1H, J=8, 1 Hz), 5.63 (ddt, 1H, J=17, 10, 7 Hz), 5.00 (dm, 1H, J=17 Hz),4.97 (dm, 1H, J=10 Hz) 3.42-3.34 (m, 1H), 3.00-2.90 (m, 2H), 2.61 (s, 3H), 2.56 (dtm, 1H, J=14, 6 Hz), 2.36 (dtm, 1H, J=14, 7 Hz). Mass spectrum (NH3 /CI): m/z=350 (M+1).

Workup

  1. extractionThe mixture was extracted with 5 mL of ethyl acetate
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. customdecanted
  4. customevaporated
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluting with 10-20% ethyl ether in hexane

Sources & evidence

ORD record
ord-1cd633090612478788375293786312df
Source dataset
uspto-grants-1999_10
Patent number
US05962462

Reaction notes

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