Hexanoyl chloride → HCID 18544096, compound

HRID 1268130Notes

Reaction equation

HRID 1268130 reaction equation
[C:1](Cl)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:9]([O:16][C:17]1[CH:18]=[C:19]([CH:33]=[CH:34][CH:35]=1)[C:20]([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29](=[O:32])(=[O:31])[NH2:30])=[O:21])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]>CN(C)C1C=CN=CC=1.O1CCCC1>[CH2:9]([O:16][C:17]1[CH:18]=[C:19]([CH:33]=[CH:34][CH:35]=1)[C:20]([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29]([NH:30][C:1](=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])(=[O:32])=[O:31])=[O:21])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 2

HCID 67340Hexanoyl chlorideHCID 18544091HCID 18544091, compound

Product 1

HCID 18544096HCID 18544096, compoundYield 84.4%

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 390 mg (1.00 mmol) of 3-heptyloxy-N-(2-sulfamoylphenyl)benzamide produced in Reference Example 9 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 412 mg (yield: 84.4%) 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-2ce09d9c2c7245c0b68af11da9b20161
Source dataset
uspto-grants-2003_04
Patent number
US06555584B1

Reaction notes

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