Benzoyl chloride → HCID 12041305, compound

HRID 1268098Notes

Reaction equation

HRID 1268098 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:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[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:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=[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 7412Benzoyl chlorideHCID 25517Ammonium ChlorideHCID 12041307HCID 12041307, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 12041305HCID 12041305, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a stream of nitrogen and under ice-cooling, 88 mg (0.78 mmol) of potassium t-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 111 mg (0.78 mmol) of benzoyl 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 247 mg (yield: 65%) 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-01414ce659394693a98e21671c618fcf
Source dataset
uspto-grants-2003_04
Patent number
US06555584B1

Reaction notes

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