Sodium hydride → HCID 18960404, compound

HRID 1707934Notes

Reaction equation

HRID 1707934 reaction equation
[CH3:1][C:2]([NH:5][S:6]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])[CH3:3].[H-].[Na+].Br[CH2:21][CH2:22][O:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][O:25]1.[NH4+].[Cl-]>CN(C=O)C.O>[CH3:4][C:2]([NH:5][S:6]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:21][CH2:22][O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[CH:10]=1)(=[O:8])=[O:7])([CH3:1])[CH3:3]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 18960407HCID 18960407, compound

Product 1

HCID 18960404HCID 18960404, compoundYield 86.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 5.0 g (0.020 mol) of N-(1,1-dimethylethyl)-1H-indole-3-sulfonamide in 30 mL anhydrous DMF was cooled to 10° C. under nitrogen atmosphere and was treated slowly with 0.87 g (0.022 mol) 60% sodium hydride (oil dispersion). The mixture was stirred for 20 minutes at room temperature then recooled to 10° C., whereupon 5.0 g (0.024 mol) of 2-(2'-bromoethoxy)tetrahydropyran (J. Org. Chem., Vol. 50, p. 4243, 1985) was added followed by heating to 70° C. for 3 hours. After cooling in an ice bath, 20 mL of saturated NH4Cl solution plus 20 mL of water was added and the mixture was extracted twice with ethyl acetate. The organic extract was washed twice with dilute HCl solution, then brine followed by drying (MgSO4) and evaporation in vacuo. The residue was triturated and collected by filtration with n-butyl chloride to afford 6.61 g of the title compound, m.p. 125°-132° C.

Workup

  1. additionwas added
  2. temperatureby heating to 70° C. for 3 hours
  3. temperatureAfter cooling in an ice bath
  4. extractionthe mixture was extracted twice with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed twice with dilute HCl solution
  7. customby drying
  8. custom(MgSO4) and evaporation in vacuo
  9. customThe residue was triturated
  10. filtrationcollected by filtration with n-butyl chloride

Sources & evidence

ORD record
ord-f35556a727024349a2a5ad029fd0fe6e
Source dataset
uspto-grants-1994_10
Patent number
US05356862

Reaction notes

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