Sulfuric Acid → HCID 18457039, compound

HRID 1272389Notes

Reaction equation

HRID 1272389 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)([CH:11]([CH3:13])[CH3:12])[C:9]#[N:10])=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:22].[OH-].[NH4+]>C(O)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:14]2[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=2)([CH:11]([CH3:13])[CH3:12])[C:9]([NH2:10])=[O:22])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 18457040HCID 18457040, compound

Product 1

HCID 18457039HCID 18457039, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2,2-Bis-(4-fluoro-phenyl)-3-methyl-butyronitrile (2.21 g) was suspended in acetic acid (2 ml) and conc. sulphuric acid (2 ml) and heated to 130° C. for 1.5 hrs. The reaction mixture was poured onto ice/water and the pH adjusted to 9 with aq. ammonium hydroxide. The mixture was extracted with dichloromethane (3×), washed with water (2×) and brine, dried (MgSO4), filtered and concentrated. The product was taken up in dichloromethane and triturated with cold hexane to precipitate the title compound (50%; M.p. 142.3–147.0° C.).

Workup

  1. additionThe reaction mixture was poured onto ice/water
  2. extractionThe mixture was extracted with dichloromethane (3×)
  3. washwashed with water (2×) and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customtriturated with cold hexane
  8. customto precipitate the title compound (50%; M.p. 142.3–147.0° C.)

Sources & evidence

ORD record
ord-68ff8a80980846e7885edc2d358122c7
Source dataset
uspto-grants-2007_04
Patent number
US07208527B2

Reaction notes

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