Potassium Carbonate → HCID 58107403, compound

HRID 873648Notes

Reaction equation

HRID 873648 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:16])[C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[S:17]([N:20]=CN(C)C)(=[O:19])=[O:18].C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:16])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:32][CH2:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[S:17]([NH2:20])(=[O:19])=[O:18]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 12503(3-Bromopropyl)benzeneHCID 66850297HCID 66850297, compound

Product 1

HCID 58107403HCID 58107403, compoundYield 3.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

2-Chloro-N-dimethylaminomethylene-5-(4-hydroxy-benzoyl)-benzenesulfonamide (250 mg, 0.68 mmol) is dissolved in N,N,-dimethylformamide (5 mL). Potassium carbonate (235 mg, 1.7 mmol) is then added followed by (3-bromo-propyl)-benzene (135 mg, 0.68 mmol). The reaction is heated to 65° C. for 18 hours. The reaction mixture is diluted with water and extracted with ethyl acetate, the organic layer is separated and concentrated in vacuo. The crude ether is purified by column chromatography (gradient of ethyl acetate in hexanes 25-75%). The residue is dissolved in ethanol (3 mL), treated with concentrated HCl (400 μl) and heated to reflux for 2.5 hours after which the reaction is allowed to cool to ambient temperature overnight. The volatiles were removed in vacuo and the crude sulfonamide is purified by column chromatography (gradient of ethyl acetate in hexanes 20-70%) affording 10 mg of the title compound. 1H NMR (DMSO) 2.02-2.11 (m, 2H), 2.76 (t, 2H, J=7.16 Hz), 4.10 (t, 2H, J=6.41 Hz), 7.10 (d, 2H, J=8.67 Hz), 7.17-7.32 (m, 7.75-7.91 (m, 6H), 8.24 (d, 1H, J=1.88 Hz). MS (m/z): 430 (M+1).

Workup

  1. extractionextracted with ethyl acetate
  2. customthe organic layer is separated
  3. concentrationconcentrated in vacuo
  4. customThe crude ether is purified by column chromatography (gradient of ethyl acetate in hexanes 25-75%)
  5. dissolutionThe residue is dissolved in ethanol (3 mL)
  6. additiontreated with concentrated HCl (400 μl)
  7. temperatureheated
  8. temperatureto reflux for 2.5 hours after which the reaction
  9. temperatureto cool to ambient temperature overnight
  10. customThe volatiles were removed in vacuo
  11. customthe crude sulfonamide is purified by column chromatography (gradient of ethyl acetate in hexanes 20-70%)

Sources & evidence

ORD record
ord-e9c82ac48c114866b78f6c7f8de5451d
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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