Sodium hydride → HCID 13922894, compound

HRID 2232374Notes

Reaction equation

HRID 2232374 reaction equation
Cl.[CH3:2][N:3]([CH3:7])[CH2:4][CH2:5][SH:6].[H-].[Na+].Br[CH2:11][C:12]1[CH:24]=[CH:23][C:15]2[S:16][C:17]([S:19](=[O:22])(=[O:21])[NH2:20])=[CH:18][C:14]=2[CH:13]=1>CN(C=O)C>[CH3:2][N:3]([CH3:7])[CH2:4][CH2:5][S:6][CH2:11][C:12]1[CH:24]=[CH:23][C:15]2[S:16][C:17]([S:19](=[O:21])(=[O:22])[NH2:20])=[CH:18][C:14]=2[CH:13]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 25798Captamine HydrochlorideHCID 13922868HCID 13922868, compound

Product 1

HCID 13922894HCID 13922894, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of 2-dimethylaminoethanethiol hydrochloride (14.17 g, 0.10 mol) in 125 ml of dry DMF was added portionwise 60% sodium hydride in mineral oil (8.0 g, 0.2 mol) under a nitrogen atmosphere over 1/2 hour with warming on the steam bath. The mixture was stirred an additional 1/2 hour and then cooled in ice. To the cold suspension was added dropwise a solution of 5-bromomethyl-2-sulfamoylbenzo[b]thiophene (7.66 g, 0.025 mol) in 25 ml of DMF. The mixture was stirred for an additional 1 hour at ice bath temperature. The mixture was filtered and the filtrate was concentrated in vacuo at 0.5 mm at room temperature. The solid residue was combined with the filtered solid and was dissolved in 3N HCl (100 ml). The acid solution was extracted with CHCl3 (3×50 ml), neutralized with NaHCO3 and concentrated to dryness in vacuo. The residual solid was extracted with CHCl3 (3×100 ml). The CHCl3 extracts were dried over anhydrous Na2SO4, filtered and concentrated in vacuo at room temperature. The solid obtained contained some polar inpurity which was removed by trituration with hot water. There was recovered 2.8 g of product (Yield 34%); m.p. 132-133%.

Workup

  1. temperaturewith warming on the steam bath
  2. temperaturecooled in ice
  3. stirringThe mixture was stirred for an additional 1 hour at ice bath temperature
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated in vacuo at 0.5 mm at room temperature
  6. dissolutionwas dissolved in 3N HCl (100 ml)
  7. extractionThe acid solution was extracted with CHCl3 (3×50 ml)
  8. concentrationconcentrated to dryness in vacuo
  9. extractionThe residual solid was extracted with CHCl3 (3×100 ml)
  10. dry with materialThe CHCl3 extracts were dried over anhydrous Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo at room temperature
  13. customThe solid obtained
  14. customwas removed by trituration with hot water

Sources & evidence

ORD record
ord-6c83a9aa79bd467e8a8b2ced73feca86
Source dataset
uspto-grants-1988_11
Patent number
US04788192

Reaction notes

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