Ethanol → HCID 68486368, compound

HRID 389018Notes

Reaction equation

HRID 389018 reaction equation
S(Cl)(Cl)=O.Cl.[CH3:6][N:7]1[CH2:12][CH2:11][C:10](=[C:13]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH2:20][CH2:19][C:18]3[S:17][C:16]([C:27]([OH:29])=[O:28])=[CH:15][C:14]2=3)[CH2:9][CH2:8]1.[CH2:30](O)[CH3:31]>>[CH3:6][N:7]1[CH2:8][CH2:9][C:10](=[C:13]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH2:20][CH2:19][C:18]3[S:17][C:16]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:15][C:14]2=3)[CH2:11][CH2:12]1

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 68491029HCID 68491029, compound

Product 1

HCID 68486368HCID 68486368, compoundYield 100%

Procedure

Ethanol (10 mL) was chilled to 0° C., and thionyl chloride (0.24 mL, 0.32 mmol) was added dropwise. Compound 4 (100 mg, 0.29 mmol) was added to the solution, and the mixture was stirred for 30 minutes, and then refluxed while heating for 2 hours. After allowing the refluxed mixture to cool in the air, the solvents were distilled off under a reduced pressure, and the precipitated crystals were separated by filtration and dried, to give 107 mg (100%) of the captioned compound in the form of white crystals.

Workup

  1. temperaturerefluxed
  2. temperaturewhile heating for 2 hours
  3. temperatureto cool in the air
  4. distillationthe solvents were distilled off under a reduced pressure
  5. customthe precipitated crystals were separated by filtration
  6. customdried

Sources & evidence

ORD record
ord-9b30c7700ae14c50b61268ad62a6a366
Source dataset
uspto-grants-2013_02
Patent number
US08377967B2

Reaction notes

Loading…