Decanoyl chloride → N-[2-(3-Benzyloxy-4-nitrobenzamido)benzenesulfonyl]decanamide

HRID 1268107Notes

Reaction equation

HRID 1268107 reaction equation
[C:1](Cl)(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH2:13]([O:20][C:21]1[CH:22]=[C:23]([CH:37]=[CH:38][C:39]=1[N+:40]([O-:42])=[O:41])[C:24]([NH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33](=[O:36])(=[O:35])[NH2:34])=[O:25])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C1C=CN=CC=1.O1CCCC1>[CH2:13]([O:20][C:21]1[CH:22]=[C:23]([CH:37]=[CH:38][C:39]=1[N+:40]([O-:42])=[O:41])[C:24]([NH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33]([NH:34][C:1](=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])(=[O:36])=[O:35])=[O:25])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 66982Decanoyl chlorideHCID 120413133-Benzyloxy-4-nitro-N-(2-sulfamoylphenyl)benzamide

Product 1

HCID 12041314N-[2-(3-Benzyloxy-4-nitrobenzamido)benzenesulfonyl]decanamideYield 83%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a stream of nitrogen and at 0° C., 0.24 ml (1.16 mmol) of decanoyl chloride was added to an anhydrous tetrahydrofuran (10 ml) solution containing 435 mg (1.02 mmol) of 3-benzyloxy-4-nitro-N-(2-sulfamoylphenyl)benzamide produced in Reference Example 3 and 274 mg (2.23 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: 83.0%) 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-32b99491cdef4766bc8d308187c62f21
Source dataset
uspto-grants-2003_04
Patent number
US06555584B1

Reaction notes

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