Ammonium Chloride → HCID 18544107, compound

HRID 1268100Notes

Reaction equation

HRID 1268100 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH:31]=[CH:32][CH:33]=1)[C:18]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[S:27]([NH2:30])(=[O:29])=[O:28])=[O:19])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:34](Cl)(=[O:40])[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39].[Cl-].[NH4+]>O1CCCC1>[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH:31]=[CH:32][CH:33]=1)[C:18]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[S:27]([NH:30][C:34](=[O:40])[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])(=[O:29])=[O:28])=[O:19])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 67340Hexanoyl chlorideHCID 12041307HCID 12041307, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18544107HCID 18544107, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a stream of nitrogen and under ice-cooling, 210 mg (1.67 mmol) of potassium tert-butoxide was added to an anhydrous tetrahydrofuran (10 ml) solution containing 300 mg (0.78 mmol) of 2-(3-benzyloxybenzamido)benzenesulfonamide produced in Reference Example 1, and the mixture was stirred for 1 hour. This solution was mixed with 176 mg (1.19 mmol) of n-hexanoyl chloride and stirred at room temperature for 3 hours. After completion of the reaction, this was neutralized by adding an ammonium chloride aqueous solution and then the solvent was evaporated. The resulting residue was extracted with ethyl acetate, washed with water and saturated brine 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 300 mg (yield: 86%) of the title compound.

Workup

  1. temperatureIn a stream of nitrogen and under ice-cooling
  2. customproduced in Reference Example 1
  3. stirringstirred at room temperature for 3 hours
  4. customAfter completion of the reaction
  5. customthe solvent was evaporated
  6. extractionThe resulting residue was extracted with ethyl acetate
  7. washwashed with water and saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent was evaporated under a reduced pressure
  10. customThe resulting residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-b6eebecc956b44cd9f82cd0644d38277
Source dataset
uspto-grants-2003_04
Patent number
US06555584B1

Reaction notes

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