Phenyl chloroformate → HCID 18544111, compound

HRID 1268139Notes

Reaction equation

HRID 1268139 reaction equation
[C:1](Cl)(=[O:9])[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:11]([O:18][C:19]1[CH:20]=[C:21]([CH:35]=[CH:36][CH:37]=1)[C:22]([NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31](=[O:34])(=[O:33])[NH2:32])=[O:23])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C)C1C=CN=CC=1.O1CCCC1>[CH2:11]([O:18][C:19]1[CH:20]=[C:21]([CH:35]=[CH:36][CH:37]=1)[C:22]([NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31]([NH:32][C:1]([O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:9])(=[O:34])=[O:33])=[O:23])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 15891Phenyl chloroformateHCID 12041307HCID 12041307, compound

Product 1

HCID 18544111HCID 18544111, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a stream of nitrogen and at 0° C., 0.36 ml (2.87 mmol) of phenyl chlorocarbonate was added to an anhydrous tetrahydrofuran (10 ml) solution containing 1 g (2.60 mmol) of 3-benzyloxy-N-(2-sulfamoylphenyl)benzamide produced in Reference Example 1 and 702 mg (5.75 mmol) of 4-dimethylaminopyridine, the mixture was stirred at room temperature for 1 hour and then the solvent was evaporated under 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 recrystallized from acetonitrile to obtain 1.00 g (yield: 77.0%) of the title compound.

Workup

  1. customthe solvent was evaporated under 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 recrystallized from acetonitrile

Sources & evidence

ORD record
ord-0fdd9fa745c04d8aa71a118e2cac4ea5
Source dataset
uspto-grants-2003_04
Patent number
US06555584B1

Reaction notes

Loading…