Decanoyl chloride → HCID 12041324, compound

HRID 1268125Notes

Reaction equation

HRID 1268125 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].[C:13]([C:17]1[CH:43]=[CH:42][C:20]([CH2:21][O:22][C:23]2[CH:24]=[C:25]([CH:39]=[CH:40][CH:41]=2)[C:26]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[S:35](=[O:38])(=[O:37])[NH2:36])=[O:27])=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14]>CN(C)C1C=CN=CC=1>[C:13]([C:17]1[CH:43]=[CH:42][C:20]([CH2:21][O:22][C:23]2[CH:24]=[C:25]([CH:39]=[CH:40][CH:41]=2)[C:26]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[S:35]([NH:36][C:1](=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])(=[O:37])=[O:38])=[O:27])=[CH:19][CH:18]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 66982Decanoyl chlorideHCID 120413093-(4-t-Butylbenzyloxy)-N-(2-sulfamoylphenyl)benzamide

Product 1

HCID 12041324HCID 12041324, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In a stream of nitrogen and at 0° C., 0.24 ml (1.10 mmol) of decanoyl chloride was added to an anhydrous tetrahydrofuan (10 ml) solution containing 438 mg (1.00 mmol) of 3-(4-t-butylbenzyloxy)-N-(2-sulfamoylphenyl)benzamide produced in Reference Example 2 and 249 mg (2.00 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 535 mg (yield: 99.0%) 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-8ce28eac0a6a415aae22404422563b35
Source dataset
uspto-grants-2003_04
Patent number
US06555584B1

Reaction notes

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