Sodium hydride → HCID 23364254, compound

HRID 1081493Notes

Reaction equation

HRID 1081493 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]1[CH:24]=[CH:23][C:9]2[NH:10][C:11](=[O:22])[N:12]([CH2:13][CH2:14][N:15]([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])[C:8]=2[CH:7]=1)[CH3:4].[CH3:25][O:26][C:27]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:28]=1[S:35](Cl)(=[O:37])=[O:36]>C1COCC1>[CH2:3]([O:5][C:6]1[CH:24]=[CH:23][C:9]2[N:10]([S:35]([C:28]3[CH:29]=[CH:30][C:31]([O:33][CH3:34])=[CH:32][C:27]=3[O:26][CH3:25])(=[O:37])=[O:36])[C:11](=[O:22])[N:12]([CH2:13][CH2:14][N:15]([CH:16]([CH3:18])[CH3:17])[CH:19]([CH3:21])[CH3:20])[C:8]=2[CH:7]=1)[CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27346262,4-Dimethoxybenzenesulfonyl chlorideHCID 22922517HCID 22922517, compound

Product 1

HCID 23364254HCID 23364254, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.05 g of sodium hydride as a 60% dispersion in oil is added in portions to a solution of 0.5 g of 5-ethoxy-1,3-dihydro-3-[2-(N,N-diisopropylamino)ethyl]-2H-benzimidazol-2-one in 7 ml of THF and the mixture is stirred for 30 minutes at RT. 0.42 g of 2,4-dimethoxybenzenesulfonyl chloride is then added and the mixture is stirred for 1 hour at RT. The solvent is evaporated off under vacuum, the residue is taken up with water, extracted with AcOEt, washed with water and dried over Na2SO4 and the solvent is evaporated off under vacuum to give 0.7 g of the expected product after crystallization from iso ether. M.p.=132° C.

Workup

  1. stirringthe mixture is stirred for 1 hour at RT
  2. customThe solvent is evaporated off under vacuum
  3. extractionextracted with AcOEt
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-661575cc960d481bb389c454f2ad11c7
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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