Sodium hydride → HCID 23364280, compound

HRID 1081509Notes

Reaction equation

HRID 1081509 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]1[CH:21]=[CH:20][C:9]2[NH:10][C:11](=[O:19])[N:12]([C:13]([CH3:18])([CH3:17])[CH2:14][O:15][CH3:16])[C:8]=2[CH:7]=1)[CH3:4].[CH3:22][O:23][C:24]([C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[C:28]([O:36][CH3:37])[CH:27]=1)=[O:25]>C1COCC1>[CH2:3]([O:5][C:6]1[CH:21]=[CH:20][C:9]2[N:10]([S:32]([C:29]3[CH:30]=[CH:31][C:26]([C:24]([O:23][CH3:22])=[O:25])=[CH:27][C:28]=3[O:36][CH3:37])(=[O:34])=[O:33])[C:11](=[O:19])[N:12]([C:13]([CH3:17])([CH3:18])[CH2:14][O:15][CH3:16])[C:8]=2[CH:7]=1)[CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 23364278162141-56-2HCID 54017342HCID 54017342, compound

Product 1

HCID 23364280HCID 23364280, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.12 g of sodium hydride as a 60% dispersion in oil is added in portions to a mixture of 1 g of 5- ethoxy-1,3-dihydro-3-(2-methoxy-1,1-dimethylethyl)-2H-benzimidazol-2-one and 30 ml of THF and the mixture is stirred for 30 minutes at RT. 1.2 g of 4-methoxycarbonyl-2-methoxybenzenesulfonyl chloride are then added and the mixture is stirred for 2 hours at RT. It is concentrated under vacuum, the residue is extracted with AcOEt, washed with water and dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using a DCM/AcOEt mixture (98/2; v/v) as the eluent to give 1.7 g of the expected product, which is used as such in the next step.

Workup

  1. stirringthe mixture is stirred for 2 hours at RT
  2. concentrationIt is concentrated under vacuum
  3. extractionthe residue is extracted with AcOEt
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. customthe solvent is evaporated off under vacuum
  7. customThe residue is chromatographed on silica using a DCM/AcOEt mixture (98/2; v/v) as the eluent

Sources & evidence

ORD record
ord-02707bd6c3e848d692cc0a8c3daf09b4
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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