Hexanoyl chloride → N-[2-(3-Cyclohexylmethoxybenzamido)benzenesulfonyl]hexanamide

HRID 1268121Notes

Reaction equation

HRID 1268121 reaction equation
[C:1](Cl)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH:9]1([CH2:15][O:16][C:17]2[CH:18]=[C:19]([CH:33]=[CH:34][CH:35]=2)[C:20]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[S:29](=[O:32])(=[O:31])[NH2:30])=[O:21])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>CN(C)C1C=CN=CC=1.O1CCCC1>[CH:9]1([CH2:15][O:16][C:17]2[CH:18]=[C:19]([CH:33]=[CH:34][CH:35]=2)[C:20]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[S:29]([NH:30][C:1](=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])(=[O:32])=[O:31])=[O:21])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 67340Hexanoyl chlorideHCID 120413213-Cyclohexylmethoxy-N-(2-sulfamoylphenyl)benzamide

Product 1

HCID 12972894N-[2-(3-Cyclohexylmethoxybenzamido)benzenesulfonyl]hexanamideYield 100.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a stream of nitrogen and at 0° C., 0.16 ml (1.10 mmol) of hexanoyl chloride was added to an anhydrous tetrahydrofuran (10 ml) solution containing 400 mg (1.00 mmol) of 3-cyclohexylmethoxy-N-(2-sulfamoylphenyl)benzamide produced in Reference Example 7 and 237 mg (1.90 mmol) of 4-dimethylaminopyridine, the mixture was stirred at room temperature for 1 hour and then the solvent was evaporated under a reduced pressure. The resulting residue was dissolved in ethyl acetate, washed with water, a potassium hydrgensulfate aqueous solution and saturated brine in that order and dried over anhydrous sodium sulfate, and then the solvent was evaporated under a reduced pressure. The resulting residue was purified by a silica gel column chromatography to obtain 490 mg (yield: 97.8%) of the title compound.

Workup

  1. customthe solvent was evaporated under a reduced pressure
  2. dissolutionThe resulting residue was dissolved in ethyl acetate
  3. washwashed with water
  4. dry with materiala potassium hydrgensulfate aqueous solution and saturated brine in that order and dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under a reduced pressure
  6. customThe resulting residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-916d803ebb7f4b4a9565f6a67d96dba5
Source dataset
uspto-grants-2003_04
Patent number
US06555584B1

Reaction notes

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