Hydrochloric Acid → 3'-Fluoro-4'-(hexadecylamino)-2-(phenylsulfonyl)acetophenone

HRID 1156133Notes

Reaction equation

HRID 1156133 reaction equation
[H-].[Na+].[CH3:3][S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:6])=[O:5].[F:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=1[NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[C:17](OC)=[O:18].Cl>O1CCCC1.COCCOC>[F:13][C:14]1[CH:15]=[C:16]([C:17](=[O:18])[CH2:3][S:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH:21]=[CH:22][C:23]=1[NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 18369Methyl phenyl sulfoneHCID 24758Sodium hydrideHCID 20536536Methyl 3-fluoro-4-(hexadecylamino)benzoate

Product 1

HCID 205365413'-Fluoro-4'-(hexadecylamino)-2-(phenylsulfonyl)acetophenone

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 864 mg. of sodium hydride and 5.3 g. of methylphenylsulfone in 20 ml. of 1,2-dimethoxyethane is stirred at 60° C. for one hour under an atmosphere of argon. To this solution is then added a solution of 5.0 g. of methyl 3-fluoro-4-(hexadecylamino)benzoate and 50 ml. of tetrahydrofuran and the reaction mixture is stirred at 60° C. for 1.5 hours. The mixture is cooled, poured onto ice, acidified with dilute hydrochloric acid to pH 3 and then extracted with chloroform. The organic layer is separated, washed three times with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated to dryness. The crude solid is chromatographed on silica gel, eluting with methylene chloride to yield 3'-fluoro-4'-(hexadecylamino)-2-(phenylsulfonyl)acetophenone.

Workup

  1. additionTo this solution is then added a solution of 5.0 g
  2. temperatureThe mixture is cooled
  3. additionpoured onto ice
  4. extractionextracted with chloroform
  5. customThe organic layer is separated
  6. washwashed three times with water and saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated to dryness
  9. customThe crude solid is chromatographed on silica gel
  10. washeluting with methylene chloride

Sources & evidence

ORD record
ord-859d2bf3d47b4a0e98105fe4c53d7b04
Source dataset
uspto-grants-1982_06
Patent number
US04333940

Reaction notes

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