Hydrochloric Acid → 2,4-Dichloro-N-{1-[4-(propylsulphonyl)phenyl]prop-2-en-1-yl}benzamide

HRID 1698512Notes

Reaction equation

HRID 1698512 reaction equation
CC(S([NH:7][CH:8]([C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH2:20][CH2:21][CH3:22])(=[O:19])=[O:18])=[CH:13][CH:12]=1)[CH:9]=[CH2:10])=O)(C)C.Cl.C(N(CC)CC)C.[Cl:31][C:32]1[CH:40]=[C:39]([Cl:41])[CH:38]=[CH:37][C:33]=1[C:34](Cl)=[O:35]>CO>[Cl:31][C:32]1[CH:40]=[C:39]([Cl:41])[CH:38]=[CH:37][C:33]=1[C:34]([NH:7][CH:8]([C:11]1[CH:12]=[CH:13][C:14]([S:17]([CH2:20][CH2:21][CH3:22])(=[O:18])=[O:19])=[CH:15][CH:16]=1)[CH:9]=[CH2:10])=[O:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 666452,4-Dichlorobenzoyl chlorideHCID 672757392-Methyl-N-{1-[4-(propylsulphonyl)phenyl]prop-2-en-1-yl}propane-2-sulphinamide

Product 1

HCID 672759492,4-Dichloro-N-{1-[4-(propylsulphonyl)phenyl]prop-2-en-1-yl}benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Methyl-N-{1-[4-(propylsulphonyl)phenyl]prop-2-en-1-yl}propane-2-sulphinamide (213 mg, 0.62 mmol) was dissolved in methanol. Methanolic hydrogen chloride was added and the reaction mixture was stirred at room temperature for 2 h. Following concentration in vacuo the residue was suspended in dichloromethane and stirred under nitrogen. Triethylamine (0.173 mL, 1.24 mmol) was added followed by 2,4-dichlorobenzoyl chloride (87 μL, 0.62 mmol) and the reaction mixture was stirred overnight. The reaction was quenched by addition of water and satd. NaHCO3(aq). The product was extracted into ethyl acetate (×2) and then the combined organic layers washed with brine, dried (MgSO4) and concentrated. 1H NMR 5 (400 MHz, CDCl3) δ 0.99 (3H, t, J=7.4 Hz), 1.66-1.76 (2H, m), 3.00-3.04 (2H, m), 5.30-5.37 (2H, m), 5.86 (1H, t, J=6.9 Hz), 6.02-6.10 (1H, m), 7.19 (1H, d, J=7.9 Hz), 7.29 (1H, dd, J=8.5, 2.1 Hz), 7.40 (1H, d, J=1.9 Hz), 7.56 (2H, dd, J=8.3, 2.5 Hz), 7.83 (2H, d, J=8.3 Hz).

Workup

  1. concentrationconcentration in vacuo the residue
  2. stirringstirred under nitrogen
  3. stirringthe reaction mixture was stirred overnight
  4. customThe reaction was quenched by addition of water
  5. extractionThe product was extracted into ethyl acetate (×2)
  6. washthe combined organic layers washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3ac98bf6a972449ba1cd418cec8ae3e2
Source dataset
uspto-grants-2012_04
Patent number
US08163956B2

Reaction notes

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