Potassium Carbonate → N-[(cyclohexylamino)carbonyl]-3-[3-(4-phenoxy-2-propylphenoxy)propoxy]benzenesulfonamide

HRID 2251735Notes

Reaction equation

HRID 2251735 reaction equation
[O:1]([C:8]1[CH:28]=[CH:27][C:11]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:18]=[C:19]([S:23]([NH2:26])(=[O:25])=[O:24])[CH:20]=[CH:21][CH:22]=2)=[C:10]([CH2:29][CH2:30][CH3:31])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH:38]1([N:44]=[C:45]=[O:46])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>CC(C)=O>[CH:38]1([NH:44][C:45]([NH:26][S:23]([C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([O:16][CH2:15][CH2:14][CH2:13][O:12][C:11]3[CH:27]=[CH:28][C:8]([O:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:9][C:10]=3[CH2:29][CH2:30][CH3:31])[CH:18]=2)(=[O:24])=[O:25])=[O:46])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18502Cyclohexyl isocyanateHCID 586471293-[3-(4-Phenoxy-2-propylphenoxy)propoxy]benzenesulfonamide

Product 1

HCID 10053686N-[(cyclohexylamino)carbonyl]-3-[3-(4-phenoxy-2-propylphenoxy)propoxy]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 3-[3-(4-phenoxy-2-propyl phenoxy)propoxy]benzenesulfonamide (0.04 g, 0.0906 mmol) and acetone (3 mL) was added potassium carbonate (0.025 g, 0.181 mmol). To the resulting suspension was added cyclohexyl isocyanate (0.023 mL, 0.181 mmol) dropwise. The reaction suspension was then stirred in a 65° C. oil bath for 5 h. After cooling to room temperature, the reaction was concentrated to a residue. The residue was partitioned between ethyl acetate and water. The ethyl acetate phase was dried over sodium sulfate, filtered, and concentrated to an oil. The oil was chromatographed over silica gel with hexanes/ethyl acetate (4:1) and hexanes/ethyl acetate (3:1) to afford the title compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction was concentrated to a residue
  3. customThe residue was partitioned between ethyl acetate and water
  4. dry with materialThe ethyl acetate phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. customThe oil was chromatographed over silica gel with hexanes/ethyl acetate (4:1) and hexanes/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-0c9dae6624e04c3485932b706763af28
Source dataset
uspto-grants-2008_01
Patent number
US07319170B2

Reaction notes

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