Dichloromethane → HCID 18516248, compound

HRID 1977432Notes

Reaction equation

HRID 1977432 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]([O:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[C:6]2[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[S:8][C:7]=12.C(Cl)Cl.C([O-])([O-])=[O:27].[K+].[K+]>C(OC(=O)C)(=O)C.CN(C=O)C.O>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][C:5]2[C:6]3[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[S:8][C:7]=3[C:2](=[O:27])[NH:3][CH:4]=2)=[CH:17][CH:18]=1

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 18516181HCID 18516181, compound

Product 1

HCID 18516248HCID 18516248, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of Example 311A (200 mg, 0.597 mmol) in acetic anhydride (20 mL) was heated at reflux for 18 hours. The reaction was cooled and poured over ice. The mixture was allowed to stir 1 hour before CH2Cl2 (100 mL) was added. The organic extracts were washed with 1 N NaOH (100 mL), H2O (50 mL) brine (50 mL), dried (Na2SO4), filtered and rotoevaporated to afford a crude brown residue. This residue was directly dissolved in DMF (20 mL) and H2O (3 mL), treated with K2CO3 and warmed to 60° C. for 2 hours. The reaction was allowed to cool to room temperature and then was rotoevaporated. The crude residue was purified by column chromatography on silica gel eluting with 10% ethyl acetate/hexane with a gradient to 50% ethyl acetate/hexane to provide the title compound.

Workup

  1. temperatureat reflux for 18 hours
  2. temperatureThe reaction was cooled
  3. additionpoured over ice
  4. additionwas added
  5. washThe organic extracts were washed with 1 N NaOH (100 mL), H2O (50 mL) brine (50 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customto afford a crude brown residue
  9. temperatureto cool to room temperature
  10. customThe crude residue was purified by column chromatography on silica gel eluting with 10% ethyl acetate/hexane with a gradient to 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-aea1f450ea7b49eb9a799398b2c91a56
Source dataset
uspto-grants-2001_05
Patent number
US06232320B1

Reaction notes

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