Ammonium Chloride → HCID 12041308, compound

HRID 1268101Notes

Reaction equation

HRID 1268101 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](=[O:30])(=[O:29])[NH2:28])=[O:19])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:34](Cl)(=[O:44])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43].[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:28][C:34](=[O:44])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])(=[O:29])=[O:30])=[O:19])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 66982Decanoyl chlorideHCID 12041307HCID 12041307, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 12041308HCID 12041308, compoundYield 53.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a stream of nitrogen and at 0° C., 117 mg (1.04 mmol) of potassium t-butoxide was added to an anhydrous tetrahydrofuran (10 ml) solution containing 200 mg (0.52 mmol) of 3-benzyloxy-N-(2-sulfamoylphenyl)benzamide produced in Reference Example 1, and the mixture was stirred for 1 hour. Next, this solution was mixed with 0.16 ml (0.78 mmol) of decanoyl 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 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 150 mg (yield: 50.0%) of the title compound.

Workup

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

Sources & evidence

ORD record
ord-005bf164f63c4e1e83c916033a142513
Source dataset
uspto-grants-2003_04
Patent number
US06555584B1

Reaction notes

Loading…