Acetonitrile → HCID 49824235, compound

HRID 618787Notes

Reaction equation

HRID 618787 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([N:13]=[C:14]=S)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[C:18](#[N:20])[CH3:19].[CH2:21]([NH2:26])[CH2:22][CH:23]([CH3:25])[CH3:24].[S:27]([O-:31])([O-])(=O)=[O:28].[Mg+2].[CH2:33]([Cl:35])Cl>[Hg]=O.C(N(CC)CC)C>[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([NH:26][CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])=[C:19]([S:27]([C:3]2[CH:4]=[CH:5][C:33]([Cl:35])=[CH:7][CH:8]=2)(=[O:31])=[O:28])[C:18]#[N:20])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

8

Reactant 5

HCID 6342AcetonitrileHCID 6344DichloromethaneHCID 7894IsoamylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 27333953,5-Bis(trifluoromethyl)phenyl isothiocyanate

Product 1

HCID 49824235HCID 49824235, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 30856Mercuric oxideCatalystHCID 8471TriethylamineSolvent

Procedure

To a solution of 3,5-bis(trifluoromethyl)phenylisothiocyanate (1,44 g, 5.31 mmol) in DCM (15 mL) and acetonitrile (5 mL) first 4-chlorophenylsulfonylacetonitrile (1.10 g, 5.10 mmol) and then triethylamine (1.0 mL) were added. The resulting mixture was stirred at room temperature for 2 h 15 min, and then isoamylamine (0.65 mL, 5.59 mmol), mercury(II) oxide (2.70 g, 12.47 mmol) and magnesium sulfate (0.8 g) were added. Stirring was continued for 2 d. The mixture was then filtered, poured into a mixture of ice-water (200 mL) and concentrated hydrochloric acid (2 mL), phases were separated, the aqueous layer was extracted twice with DCM (20 mL) and the combined extracts were dried (magnesium sulfate) and concentrated. Column chromatography of the residue (100 g silica gel, gradient elution with heptane/ethyl acetate 10:0 to 3:1) gave 317 mg (12%) of the title compound as an oil. 1H NMR (300 MHz, DMSO-d6): δ=0.79 (d, J=7 Hz, 6H), 1.39 (q, J=7 Hz, 2H), 1.50 (nonett, J=7 Hz, 1H), 3.31 (m, 2H), 7.27 (s, 2H), 7.67-7.80 (m, 5H), 8.13 (s, br, 1H), 9.76 (s, 1H); LCMS: elution at 16.23 min, MH+ : 540.

Workup

  1. stirringStirring
  2. waitwas continued for 2 d
  3. filtrationThe mixture was then filtered
  4. additionpoured into a mixture of ice-water (200 mL) and concentrated hydrochloric acid (2 mL), phases
  5. customwere separated
  6. extractionthe aqueous layer was extracted twice with DCM (20 mL)
  7. dry with materialthe combined extracts were dried (magnesium sulfate)
  8. concentrationconcentrated
  9. washColumn chromatography of the residue (100 g silica gel, gradient elution with heptane/ethyl acetate 10:0 to 3:1)

Sources & evidence

ORD record
ord-c50fe06e350049ea86bd082ef00dccf5
Source dataset
uspto-grants-1999_09
Patent number
US05955548

Reaction notes

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