Acetic Acid → Senicapoc

HRID 1595554Notes

Reaction equation

HRID 1595554 reaction equation
S(=O)(=O)(O)O.C(O)(=[O:8])C.[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:18]#[N:19])=[CH:13][CH:12]=1.[OH-].[NH4+]>CCCCCC>[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:18]([NH2:19])=[O:8])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 24799666Bis(4-fluorophenyl)(phenyl)acetonitrile

Product 1

HCID 216327SenicapocYield 87%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
130 °C

Procedure

A solution of concentrated sulfuric acid (50 mL) and glacial acetic acid (50 mL) was added to bis(4-fluorophenyl)phenylacetonitrile (18.9 g, 0.06 mol) at rt. The resulting orange solution was stirred and heated at 130° C. for 3 h. The reaction was cooled to 0° C., poured into ice water (150 mL) and neutralized with ammonium hydroxide. The organics were extracted with chloroform (3×100 mL), combined and washed with brine (2×50 mL). The organics were dried (Na2SO4) and concentrated under reduced pressure to afford a yellow-orange solid. The solid was stirred with hot hexane (100 ml) for 30 min and filtered. Crystallization from dichloromethane/hexane gave bis(4-fluorophenyl)phenylacetamide (3) as a white crystalline solid (16.9 g, 0.052 mol, 87%).

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. extractionThe organics were extracted with chloroform (3×100 mL)
  3. washwashed with brine (2×50 mL)
  4. dry with materialThe organics were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customto afford a yellow-orange solid
  7. filtrationfiltered
  8. customCrystallization from dichloromethane/hexane

Sources & evidence

ORD record
ord-432ad823d1ae4765a5963dc98c116e4f
Source dataset
uspto-grants-2001_09
Patent number
US06288122B1

Reaction notes

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