Acetyl chloride → HCID 12041306, compound

HRID 1268099Notes

Reaction equation

HRID 1268099 reaction equation
[CH3:1][C:2](C)([O-:4])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(Cl)(=O)C.[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:2](=[O:4])[CH3:1])(=[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 6367Acetyl chlorideHCID 25517Ammonium ChlorideHCID 12041307HCID 12041307, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 12041306HCID 12041306, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a stream of nitrogen and under ice-cooling, 162 mg (1.44 mmol) of potassium t-butoxide was added to an anhydrous tetrahydrofuran (10 ml) solution containing 400 mg (1.04 mmol) of 2-(3-benzyloxybenzamido)benzenesulfonamide produced in Reference Example 1, and the mixture was stirred for 1 hour. This solution was mixed with 121 mg (1.54 mmol) of acetyl 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 160 mg (yield: 35%) 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-de7aedbd28884c2295948707a40728d9
Source dataset
uspto-grants-2003_04
Patent number
US06555584B1

Reaction notes

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