Ammonium Chloride → HCID 15020346, compound

HRID 1460231Notes

Reaction equation

HRID 1460231 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[C:5]([F:10])[CH:4]=1.[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([CH:20]2[CH2:25][CH2:24][N:23]([S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)(=[O:28])=[O:27])[CH2:22][CH2:21]2)=[O:19])=[CH:14][CH:13]=1.[Cl-].[NH4+]>O1CCCC1>[F:10][C:5]1[CH:4]=[C:3]([C:18]([C:15]2[CH:16]=[CH:17][C:12]([F:11])=[CH:13][CH:14]=2)([CH:20]2[CH2:25][CH2:24][N:23]([S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)(=[O:28])=[O:27])[CH2:22][CH2:21]2)[OH:19])[CH:8]=[CH:7][C:6]=1[F:9]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 676754-Bromo-1,2-difluorobenzeneHCID 1438176HCID 1438176, compoundHCID 5462224Magnesium

Product 1

HCID 15020346HCID 15020346, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A three-necked round bottom flask, equipped with a mechanical stirrer, flushed with nitrogen, and containing 3.74 g (0.154 mole) of magnesium turnings, was dried with a Bunsen burner. After the flask had cooled, 600 ml of tetrahydrofuran was added. To this mechanically stirred mixture was slowly added a solution of 29.4 g (0.152 mole) of 4-bromo-1,2-difluorobenzene in 50 ml of tetrahydrofuran. The mixture was stirred for 1 hour, and 45.11 g (0.13 mole) of (4-fluorophenyl)[1-(phenylsulfonyl)-4-piperidinyl]methanone was added as a solid. The solution was stirred at ambient temperatures for 3 hours and was poured into an icy aqueous solution of ammonium chloride. The aqueous mixture was extracted with methylene chloride, dried over magnesium sulfate, and the solvent was removed in vacuo. The residue was recrystallized from methylene chloridehexane to give 58.89 g (82.9%) of the title compound. A small sample was recrystallized from a mixture of methylene chloride-ether-hexane to give an analytically pure sample of the title compound, mp 97°-99° C.

Workup

  1. customA three-necked round bottom flask, equipped with a mechanical stirrer
  2. customflushed with nitrogen
  3. customwas dried with a Bunsen burner
  4. temperatureAfter the flask had cooled
  5. addition600 ml of tetrahydrofuran was added
  6. stirringThe solution was stirred at ambient temperatures for 3 hours
  7. extractionThe aqueous mixture was extracted with methylene chloride
  8. dry with materialdried over magnesium sulfate
  9. customthe solvent was removed in vacuo
  10. customThe residue was recrystallized from methylene chloridehexane

Sources & evidence

ORD record
ord-c6e5bb7ec00d4f37af7445711c90f727
Source dataset
uspto-grants-1991_12
Patent number
US05070087

Reaction notes

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