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

HRID 2251732Notes

Reaction equation

HRID 2251732 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:22]=[CH:21][C:20]([S:23]([NH2:26])(=[O:25])=[O:24])=[CH:19][CH:18]=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:20]2[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][CH:19]=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 586471284-[3-(4-Phenoxy-2-propylphenoxy)propoxy]benzenesulfonamide

Product 1

HCID 9850927N-[(cyclohexylamino)carbonyl]-4-[3-(4-phenoxy-2-propylphenoxy)propoxy]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 4-[3-(4-phenoxy-2-propyl phenoxy)propoxy]benzenesulfonamide (0.045 g, 0.102 mmol) and acetone (3 mL) was added potassium carbonate (0.028 g, 0.204 mmol). To the resulting suspension was added cyclohexyl isocyanate (0.026 mL, 0.204 mmol) dropwise. The reaction suspension was then stirred in a 65° C. oil bath for 6 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 obtain 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-8cadbd035cb24d7dbb22b5b977f2f8b2
Source dataset
uspto-grants-2008_01
Patent number
US07319170B2

Reaction notes

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