Sodium hydride → N-(1,1-Dimethylethyl)-N'-2-(4-morpholinyl)ethyl-2,5-thiophenedisulfonamide

HRID 2255496Notes

Reaction equation

HRID 2255496 reaction equation
[CH3:1][C:2]([NH:5][S:6]([C:9]1[S:10][C:11]([S:14]([NH2:17])(=[O:16])=[O:15])=[CH:12][CH:13]=1)(=[O:8])=[O:7])([CH3:4])[CH3:3].[H-].[Na+].Cl.Cl[CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>CN(C)C=O>[CH3:4][C:2]([NH:5][S:6]([C:9]1[S:10][C:11]([S:14]([NH:17][CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)(=[O:16])=[O:15])=[CH:12][CH:13]=1)(=[O:8])=[O:7])([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 14909920N-tert-Butyl-5-sulfamoylthiophene-2-sulfonamide

Product 1

HCID 19737988N-(1,1-Dimethylethyl)-N'-2-(4-morpholinyl)ethyl-2,5-thiophenedisulfonamideYield 22.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the product from Step B (1.05 g, 3.52 mmol), sodium hydride (60% dispersion in mineral oil, 310 mg, 7.75 mmol) and 4-(2-chloroethyl)morpholine hydrochloride (0.721 g, 3.88 mmol) in anhydrous dimethylformamide (DMF) (20 mL) was heated at 110° C. for 2.5 h and then stirred at ambient temperature overnight. The reaction mixture was extracted with ethyl acetate (3×100 mL), washed with brine, dried over molecular sieves and concentrated. The residue was chromatographed (silica, elution with 50% ethyl acetate-hexane) to yield 0.32 g (22%) of the desired product.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (3×100 mL)
  2. washwashed with brine
  3. customdried over molecular sieves
  4. concentrationconcentrated
  5. customThe residue was chromatographed
  6. wash(silica, elution with 50% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-2763eef046dd4f07850213c3bc9e652a
Source dataset
uspto-grants-1993_08
Patent number
US05240923

Reaction notes

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