Water → HCID 15231559, compound

HRID 1081491Notes

Reaction equation

HRID 1081491 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:20]=[CH:19][C:7]2[NH:8][C:9](=[O:18])[N:10]([CH:11]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[C:6]=2[CH:5]=1.[N+:21]([C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[C:26]([O:34][CH3:35])[CH:25]=1)([O-:23])=[O:22].O>C1COCC1>[Cl:3][C:4]1[CH:20]=[CH:19][C:7]2[N:8]([S:30]([C:27]3[CH:28]=[CH:29][C:24]([N+:21]([O-:23])=[O:22])=[CH:25][C:26]=3[O:34][CH3:35])(=[O:31])=[O:32])[C:9](=[O:18])[N:10]([CH:11]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[C:6]=2[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 3094582-Methoxy-4-nitrobenzenesulfonyl chlorideHCID 15231558HCID 15231558, compound

Product 1

HCID 15231559HCID 15231559, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

600 mg of sodium hydride as a 60% dispersion in oil were added in portions, with stirring, to a solution of 3 g of 5-chloro-3-cycloheptyl-1,3-dihydro-2H- benzimidazol-2-one in 30 ml of THF. 3 g of 4-nitro-2- methoxybenzenesulfonyl chloride were then added and the reaction mixture was stirred for 18 hours. The reaction mixture was then poured into a water+ ice mixture, extracted with ethyl acetate and washed with water and the organic phase was dried over sodium sulfate and concentrated to dryness. 3.5 g of the expected product were obtained by crystallization from an iso ether/AcOEt mixture (60/40; v/v). M.p.=193° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialthe organic phase was dried over sodium sulfate
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-17fa440da36142a9a4ba669c8ba156aa
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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