Decanoyl chloride → HCID 12041318, compound

HRID 1268115Notes

Reaction equation

HRID 1268115 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].[N+:13]([C:16]1[CH:42]=[CH:41][C:19]([CH2:20][O:21][C:22]2[CH:23]=[C:24]([CH:38]=[CH:39][CH:40]=2)[C:25]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[S:34](=[O:37])(=[O:36])[NH2:35])=[O:26])=[CH:18][CH:17]=1)([O-:15])=[O:14]>CN(C)C1C=CN=CC=1.O1CCCC1>[N+:13]([C:16]1[CH:17]=[CH:18][C:19]([CH2:20][O:21][C:22]2[CH:23]=[C:24]([CH:38]=[CH:39][CH:40]=2)[C:25]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[S:34]([NH:35][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:37])=[O:26])=[CH:41][CH:42]=1)([O-:15])=[O:14]

Participants

5

Reactant 2

HCID 66982Decanoyl chlorideHCID 12041317HCID 12041317, compound

Product 1

HCID 12041318HCID 12041318, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a stream of nitrogen and at 0° C., 0.16 ml (0.80 mmol) of decanoyl chloride was added to an anhydrous tetrahydrofuran (10 ml) solution containing 300 mg (0.70 mmol) of 3-(4-nitrobenzyloxy)-N-(2-sulfamoylphenyl)benzamide produced in Reference Example 5 and 171 mg (1.40 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 400 mg (yield: 97.9%) 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-2376c1c2c9574017ae6f2609d19291ed
Source dataset
uspto-grants-2003_04
Patent number
US06555584B1

Reaction notes

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