Dimethyl Sulfoxide → HCID 20081836, compound

HRID 1681265Notes

Reaction equation

HRID 1681265 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.CS(C)=O.[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[C:30]([CH:31]=[N:32]O)=[C:29]([CH3:34])[N:28]=[C:27]([CH:35]([CH3:37])[CH3:36])[C:26]=2[CH2:38][OH:39])=[CH:21][CH:20]=1.C(N(CC)CC)C>C(Cl)Cl>[C:31]([C:30]1[C:25]([C:22]2[CH:23]=[CH:24][C:19]([F:18])=[CH:20][CH:21]=2)=[C:26]([CH:38]=[O:39])[C:27]([CH:35]([CH3:37])[CH3:36])=[N:28][C:29]=1[CH3:34])#[N:32]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 86744712HCID 86744712, compound

Product 1

HCID 20081836HCID 20081836, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-70 °C

Procedure

4.4 g (21 mmol) of trifluoroacetic anhydride in 15 ml of methylene chloride are added dropwise at -78° C. to 1.1 g (14 mmol) of DMSO in 8 ml of methylene chloride p.A. and the mixture is stirred for 10 minutes at -70° C. 2.1 g (7 mmol) of compound 2 from Example 143 are then added in 50 ml of methylene chloride, the mixture is stirred for 1 h at -70° C. 5.8 ml (42 mmol) of triethylamine are now added and the mixture is stirred for 4 h at room temperature. It is washed with saturated sodium chloride solution, concentrated, chromatographed over 100 g of silica gel (230-400 mesh, φ 4 cm, petroleum ether/ethyl acetate 10:1) and recrystallized from ethyl acetate/petroleum ether.

Workup

  1. stirringthe mixture is stirred for 1 h at -70° C
  2. stirringthe mixture is stirred for 4 h at room temperature
  3. washIt is washed with saturated sodium chloride solution
  4. concentrationconcentrated
  5. customchromatographed over 100 g of silica gel (230-400 mesh, φ 4 cm, petroleum ether/ethyl acetate 10:1)
  6. customrecrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-553cdeaf213640f9860752f151afb410
Source dataset
uspto-grants-1992_12
Patent number
US05169857

Reaction notes

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