HCID 16102691, compound → HCID 178470120, compound

HRID 1640950Notes

Reaction equation

HRID 1640950 reaction equation
S.[Na].[Br:3][C:4]1[C:13]([O:14][CH3:15])=[C:12]2[C:7]([C:8](=[O:27])[C:9]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:10]([S:19](C)=O)[N:11]2[CH:16]2[CH2:18][CH2:17]2)=[CH:6][CH:5]=1>CN(C)C=O>[Br:3][C:4]1[C:13]([O:14][CH3:15])=[C:12]2[C:7]([C:8](=[O:27])[C:9]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:10]([SH:19])[N:11]2[CH:16]2[CH2:17][CH2:18]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 16102691HCID 16102691, compoundHCID 86586439Sodium hydrogen sulphide

Product 1

HCID 178470120HCID 178470120, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Anhydrous sodium hydrogen sulfide (Alfa Aesar, 53.3 mg, 0.95 mmol) is added in one portion to a solution of dimethylformamide (4.0 mL) containing 16 (158.1 mg, 0.37 mmol) at room temperature. The resulting solution is heated at 50° C. for 1 h and allowed to cool to room temperature. The reaction mixture is quenched by addition of a 5% aqueous solution of hydrochloric acid (50 mL) and extracted with ethyl acetate (100 mL). The organic extract is washed with brine (50 mL) and evaporated to dryness under reduced pressure to give crude ethyl 7-bromo-1-cyclopropyl-2-mercapto-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate. Rf 0 (ethyl acetate). LCMS m/z calcd for C16H1679BrNO4S ([M]+) 397. Found 398 ([M+H]+).

Workup

  1. temperatureto cool to room temperature
  2. customThe reaction mixture is quenched by addition of a 5% aqueous solution of hydrochloric acid (50 mL)
  3. extractionextracted with ethyl acetate (100 mL)
  4. extractionThe organic extract
  5. washis washed with brine (50 mL)
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-d54eaf8c49614980b33faeab04a73247
Source dataset
uspto-grants-2012_02
Patent number
US08114888B2

Reaction notes

Loading…