Water → HCID 23364255, compound

HRID 1081496Notes

Reaction equation

HRID 1081496 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]1[CH:23]=[CH:22][C:9]2[NH:10][C:11](=[O:21])[N:12]([C:13]([CH3:20])([CH3:19])[CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:8]=2[CH:7]=1)[CH3:4].[CH3:24][O:25][C:26]1[CH:31]=[C:30]([N+:32]([O-:34])=[O:33])[CH:29]=[CH:28][C:27]=1[S:35](Cl)(=[O:37])=[O:36].O>C1COCC1.CN(C=O)C>[CH2:3]([O:5][C:6]1[CH:23]=[CH:22][C:9]2[N:10]([S:35]([C:27]3[CH:28]=[CH:29][C:30]([N+:32]([O-:34])=[O:33])=[CH:31][C:26]=3[O:25][CH3:24])(=[O:36])=[O:37])[C:11](=[O:21])[N:12]([C:13]([CH3:20])([CH3:19])[CH2:14][C:15]([CH3:17])([CH3:16])[CH3:18])[C:8]=2[CH:7]=1)[CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 3094582-Methoxy-4-nitrobenzenesulfonyl chlorideHCID 22922482HCID 22922482, compound

Product 1

HCID 23364255HCID 23364255, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.2 g of sodium hydride as a 60% dispersion in oil is added in portions to a solution of 1 g of 5-ethoxy-1,3-dihydro-3-(1,1,3,3-tetramethylbutyl)-2H- benzimidazol-2-one in 10 ml of THF and 20 ml of DMF and the mixture is stirred for 30 minutes at RT. 1.2 g of 2-methoxy-4-nitrobenzenesulfonyl chloride are then added and the mixture is stirred for 5 hours at RT. The reaction mixture is poured into 200 ml of water, extracted with AcOEt, washed with water and dried over Na2SO4 and the solvent is evaporated off under vacuum to give 1.1 g of the expected product after crystallization from iso ether. M.p.=158° C.

Workup

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

Sources & evidence

ORD record
ord-da824efafad944beb41a84cc2c041117
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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