Dimethyl Sulfoxide → HCID 67820272, compound

HRID 2226058Notes

Reaction equation

HRID 2226058 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C:12]1([CH3:23])[O:16][C@@H:15]([CH2:17][CH:18]([CH3:20])[CH3:19])[C@@H:14]([CH2:21]O)[O:13]1.C(N(CC)CC)C.[CH3:31][N:32]([CH3:34])[NH2:33].S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)Cl.O>[CH3:31][N:32]([CH3:34])[N:33]=[CH:21][C@H:14]1[O:13][C:12]([CH3:23])([CH3:11])[O:16][C@H:15]1[CH2:17][CH:18]([CH3:20])[CH3:19]

Participants

9

Reactant 6

HCID 679Dimethyl SulfoxideHCID 59761,1-DimethylhydrazineHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 65578Oxalyl chlorideHCID 11745384HCID 11745384, compound

Product 1

HCID 67820272HCID 67820272, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-40 °C

Procedure

Oxalyl chloride (0.51 mL, 5.8 mmol) in 14 mL methylene chloride was cooled to -60° C. in a dry ice/chloroform bath. Dimethyl sulfoxide (0.9 mL, 11.7 mmol) in 1.0 mL methylene chloride was added and the reaction mixture was stirred for 3 minutes. The alcohol resulting from Example 8A (1.0 g, 5.31 mmol) in 2.0 mL of methylene chloride was added in one portion maintaining the temperature at -40° C. After 15 minutes, triethylamine (3.7 mL, 26.6 mmol) was added dropwise and the mixture was stirred for 5 minutes, warmed to ambient temperature, and N,N-dimethylhydrazine (1.61 mL, 1.28 g, 21.2 mmol) and magnesium sulfate (1.3 g) were added. The mixture was stirred for 1 hour at ambient temperature. Water (100 mL) was added and the organic layer was separated, washed with saturated aqueous sodium chloride, dried over magnesium sulfate, and filtered. Evaporation of the filtrate gave the hydrazone as a yellow oil. The crude hydrazone was purified by silica gel chromatography using (7:93) ethyl acetate:hexane to afford 808 mg (62%) of the title compound as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ 0.90 (d, J=6 Hz, 3H), 0.95 (d, J=6 Hz, 3H), 1.29-1.19 (m, 1H), 1.38 (s, 3H), 1.53-1.42 (m, s, 4H), 1.85-1.67 (bm, 1H), 2.82 (s, 6H), 4.33-4.25 (m, 1H), 4.6 (dd, J=7,8 Hz, 1H), 6.41 (d, J=6 Hz, 1H). MS (DCI/NH3) m/e 229 (M+H)+.

Workup

  1. waitAfter 15 minutes
  2. stirringthe mixture was stirred for 5 minutes
  3. temperaturewarmed to ambient temperature
  4. stirringThe mixture was stirred for 1 hour at ambient temperature
  5. customthe organic layer was separated
  6. washwashed with saturated aqueous sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-be98c78db1c64dd791a242d903260fef
Source dataset
uspto-grants-1994_09
Patent number
US05344990

Reaction notes

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