Acetone → HCID 117728921, compound

HRID 2200062Notes

Reaction equation

HRID 2200062 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:10]([C@@H:12]2[CH2:16][C@H:15]([N:17]([CH3:19])[CH3:18])[CH2:14][N:13]2[CH3:20])=O)=[N:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClC(Cl)(Cl)C(Cl)(Cl)Cl.CC(C)=O>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:10]([C@H:12]3[N:13]([CH3:20])[CH2:14][C@@H:15]([N:17]([CH3:19])[CH3:18])[CH2:16]3)=[N:9][N:8]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 6214HexachloroethaneHCID 11776TriphenylphosphineHCID 117729238HCID 117729238, compound

Product 1

HCID 117728921HCID 117728921, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of Intermediate 38b (1.73 g, 6.15 mmol) in THF (40 mL) was treated with triphenyl phospine (3.22 g, 12.3 mmol) and TEA (3.43 mL, 24.6 mmol). Hexachloroethane (2.91 g, 12.3 mmol) was added to the solution portion wise over a period of 5 minutes. The reaction mixture was heated at 60° C. for 16 hours. The reaction mixture was cooled down, treated with acetone to precipitate the triethylammonium chloride, which was then filtered; the filter cake was washed abundantly with acetone and the solvent was evaporated under reduced pressure. The residue was purified by SCX-2 cartridge eluting with DCM (40 mL), MeOH (40 mL) and 2M NH3 in MeOH (40 mL). The product containing fractions were evaporated under reduced pressure to give the title compound as a brown oil (1.3 g, 80%). 1H NMR (300 MHz, d6-DMSO): 201-2.13 (1H, m), 2.2 (3H, s), 2.29 (6H, s), 2.31-2.33 (1H, m), 2.34-2.39 (1H, m), 2.51-2.61 (1H, m), 2.88-2.98 (1H, m), 3.31-3.39 (1H, dd), 3.50 (1H, s), 4.17-4.27 (1H, m), 7.14-7.24 (1H, m), 7.67-7.77 (1H, m), 9.00-9.07 (1H, m).

Workup

  1. temperatureThe reaction mixture was cooled down
  2. customto precipitate the triethylammonium chloride, which
  3. filtrationwas then filtered
  4. washthe filter cake was washed abundantly with acetone
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by SCX-2 cartridge
  7. washeluting with DCM (40 mL), MeOH (40 mL) and 2M NH3 in MeOH (40 mL)
  8. additionThe product containing fractions
  9. customwere evaporated under reduced pressure

Sources & evidence

ORD record
ord-bb1d286f1df04383b1600ae8272d69ef
Source dataset
uspto-grants-2016_06
Patent number
US09359354B2

Reaction notes

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