Propargyl bromide → HCID 59552643, compound

HRID 1803808Notes

Reaction equation

HRID 1803808 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]=[C:7]([S:9]([NH2:12])(=[O:11])=[O:10])[S:8][C:4]=2[CH:3]=1.CO[CH:17](OC)[N:18]([CH3:20])[CH3:19].[H-].[Na+].[CH2:25](Br)[C:26]#[CH:27]>CN(C=O)C>[CH3:17][N:18]([CH3:20])[CH:19]=[N:12][S:9]([C:7]1[S:8][C:4]2[CH:3]=[C:2]([O:1][CH2:27][C:26]#[CH:25])[CH:14]=[CH:13][C:5]=2[N:6]=1)(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 78373Dimethylformamide dimethyl acetalHCID 68521296-Hydroxy-1,3-benzothiazole-2-sulfonamide

Product 1

HCID 59552643HCID 59552643, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 100 mL round bottomed flask equipped with a magnetic stir bar, rubber septum, and argon inlet containing DMF (25 mL) in an ice bath was placed 1 (17.5 g, 76.1 mmol) and the reaction was stirred at rt until the solid dissolved. To this solution was added N,N-dimethylformamide dimethyl acetal (60 g) and the mixture was heated at 40° C. for 4 h. Solvent was removed in vacuo at 42° C. and the residue was dissolved in anhydrous DMF (60 mL). To this solution at 0° C. was added portion wise NaH (4.56 g, 60% in oil, 114 mmol) and the reaction was stirred at 0° C. for 30 min. To this mixture was added propargyl bromide (18 g, 80% toluene solution, 121.7 mmol) dropwise. Ice bath was removed and the mixture was stirred at rt for 1 h. The residue was poured into a mixture of water and EtOAc (200 mL/200 mL). The mixture was filtered and solid was collected and dissolved in DCM (300 mL) and washed with saturated NaHCO3 (3×200 mL) and water (200 mL). To this solution was added 100 g of silica gel and dried in vacuo. The solid mixture was loaded on silica gel column and eluted with 10% EtOAc in DCM to afford compound 2 as a yellow solid (9.2 g, 37.4%).

Workup

  1. customTo a 100 mL round bottomed flask equipped with a magnetic stir bar
  2. dissolutiondissolved
  3. temperaturethe mixture was heated at 40° C. for 4 h
  4. customSolvent was removed in vacuo at 42° C.
  5. dissolutionthe residue was dissolved in anhydrous DMF (60 mL)
  6. stirringthe reaction was stirred at 0° C. for 30 min
  7. customIce bath was removed
  8. stirringthe mixture was stirred at rt for 1 h
  9. additionThe residue was poured into a mixture of water and EtOAc (200 mL/200 mL)
  10. filtrationThe mixture was filtered
  11. customsolid was collected
  12. dissolutiondissolved in DCM (300 mL)
  13. washwashed with saturated NaHCO3 (3×200 mL) and water (200 mL)
  14. additionTo this solution was added 100 g of silica gel
  15. customdried in vacuo
  16. washeluted with 10% EtOAc in DCM

Sources & evidence

ORD record
ord-efcff840adfe4aca88dc962e6cba59f1
Source dataset
uspto-grants-2013_01
Patent number
US08354092B2

Reaction notes

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