Benzene → HCID 18544118, compound

HRID 1268140Notes

Reaction equation

HRID 1268140 reaction equation
C1C=CC=CC=1.[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH:40]=[CH:41][CH:42]=1)[C:18]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[S:27]([NH:30][C:31]([O:33]C1C=CC=CC=1)=O)(=[O:29])=[O:28])=[O:19])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:43]([NH2:47])[CH2:44][CH2:45][CH3:46]>C(OCC)(=O)C>[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH:40]=[CH:41][CH:42]=1)[C:18]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[S:27]([NH:30][C:31]([NH:47][CH2:43][CH2:44][CH2:45][CH3:46])=[O:33])(=[O:29])=[O:28])=[O:19])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 8007ButylamineHCID 18544111HCID 18544111, compound

Product 1

HCID 18544118HCID 18544118, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A benzene (10 ml) solution containing 200 mg (0.40 mmol) of 3-benzyloxy-N-[2-[(phenyloxycarbonylamino)sulfonyl]phenyl]benzamide produced in Example 45 and 0.09 ml (0.88 mmol) of butylamine was heated under reflux for 2 hours. The reaction mixture 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 130 mg (yield: 68.0%) of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  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-5b169a1330024e128827c88146844404
Source dataset
uspto-grants-2003_04
Patent number
US06555584B1

Reaction notes

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