Water → HCID 15229038, compound

HRID 1081479Notes

Reaction equation

HRID 1081479 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:19]=[CH:18][C:7]2[NH:8][C:9](=[O:17])[N:10]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[C:6]=2[CH:5]=1.[CH3:20][O:21][C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:23]=1[S:31](Cl)(=[O:33])=[O:32].O>CN(C=O)C>[Cl:3][C:4]1[CH:19]=[CH:18][C:7]2[N:8]([S:31]([C:23]3[CH:24]=[CH:25][C:26]([N+:28]([O-:30])=[O:29])=[CH:27][C:22]=3[O:21][CH3:20])(=[O:32])=[O:33])[C:9](=[O:17])[N:10]([CH:11]3[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 30617906-Chloro-1-cyclohexyl-1H-benzimidazol-2-ol

Product 1

HCID 15229038HCID 15229038, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.13 g of sodium hydride as an 80% dispersion in oil was added in portions, with stirring, to a solution of 1 g of 5-chloro-3-cyclohexyl-1,3-dihydro-2H-benzimidazol-2-one in 10 ml of DMF at room temperature; 1.1 g of 2-methoxy-4-nitrobenzenesulfonyl chloride were then introduced and the reaction medium was stirred at room temperature for 4 hours. The solvent was then evaporated off under vacuum and the residue obtained was taken up with water. It was then extracted with DCM, washed with water and then dried over sodium sulfate and the solvent was evaporated off to dryness. The residue obtained was chromatographed on silica using a DCM/AcOEt mixture (95/5; v/v) as the eluent to give the expected product in the form of a slightly yellow solid, which crystallized from absolute EtOH. m=1.52 g. M.p.=185° C.

Workup

  1. customThe solvent was then evaporated off under vacuum
  2. customthe residue obtained
  3. extractionIt was then extracted with DCM
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was evaporated off to dryness
  7. customThe residue obtained
  8. customwas chromatographed on silica using a DCM/AcOEt mixture (95/5; v/v) as the eluent

Sources & evidence

ORD record
ord-c94cee2e2df446d292fea53aecc379c8
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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