Acetic Acid → HCID 21705158, compound

HRID 1595558Notes

Reaction equation

HRID 1595558 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:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)[C:18]#[N:19])=[CH:13][CH:12]=1.[OH-].[NH4+]>CCCCCC>[F:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]([C:27]2[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)[C:18]([NH2:19])=[O:8])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 21705156HCID 21705156, compound

Product 1

HCID 21705158HCID 21705158, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
130 °C

Procedure

A solution of concentrated sulfuric acid (10 mL) and glacial acetic acid (10 mL) was added to bis(4-fluorophenyl)-3-fluorophenylacetonitrile (3.18 mmol) 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 (50 mL) and neutralized with ammonium hydroxide. The organics were extracted with chloroform (3×50 mL). The organics fractions were combined washed with brine (2×20 mL), dried (Na2SO4) and concentrated under reduced pressure to afford a yellow-orange solid. The solid was stirred with hot hexane (50 ml) for 30 mins and filtered. Crystallization from dichloromethane/hexane gave the desired product bis(4-fluorophenyl)-3-fluorophenylacetamide 16 as a white crystalline solid (147 mg, 0.43 mmol, 11%, 4 steps).

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. extractionThe organics were extracted with chloroform (3×50 mL)
  3. washThe organics fractions were combined washed with brine (2×20 mL)
  4. dry with materialdried (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-c32e59277a3b473882da7c827a180d2d
Source dataset
uspto-grants-2001_09
Patent number
US06288122B1

Reaction notes

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