Sodium hydride → 5-Ethoxy-1,3-dihydro-(2-methoxy-4-benzyloxycarbonylbenzenesulfonyl)-3-cyclohexyl-2H-benzimidazol-2-one

HRID 1081485Notes

Reaction equation

HRID 1081485 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]([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[C:8]=2[CH:7]=1)[CH3:4].[CH3:22][O:23][C:24]1[CH:29]=[C:28]([C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[CH:27]=[CH:26][C:25]=1[S:40](Cl)(=[O:42])=[O:41]>C1COCC1.CN(C=O)C>[CH2:3]([O:5][C:6]1[CH:21]=[CH:20][C:9]2[N:10]([S:40]([C:25]3[CH:26]=[CH:27][C:28]([C:30]([O:32][CH2:33][C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)=[O:31])=[CH:29][C:24]=3[O:23][CH3:22])(=[O:42])=[O:41])[C:11](=[O:19])[N:12]([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[C:8]=2[CH:7]=1)[CH3:4]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 152315443-Cyclohexyl-5-ethoxy-1,3-dihydro-2H-benzimidazol-2-oneHCID 15231551Benzyl 4-chlorosulfonyl-3-methoxybenzoate

Product 1

HCID 152315525-Ethoxy-1,3-dihydro-(2-methoxy-4-benzyloxycarbonylbenzenesulfonyl)-3-cyclohexyl-2H-benzimidazol-2-oneYield 80.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.5 g of sodium hydride as a 60% dispersion in oil was added in small portions, at room temperature, to a solution of 2.4 g of 5-ethoxy-3-cyclohexyl-1,3-dihydro-2H-benzimidazol-2-one in 50 ml of THF and 50 ml of DMF and the mixture was stirred for half an hour, still at room temperature. 3.4 g of 2-methoxy-4-benzyloxycarbonylbenzenesulfonyl chloride were then added and the reaction medium was stirred for 4 hours at room temperature. It was concentrated under vacuum to remove the residual THF and the residue was taken up with water. It was then extracted with AcOEt and washed with water and the organic phase was dried over sodium sulfate and concentrated under vacuum. The residue obtained was then purified by chromatography on silica using DCM as the eluent. 4.2 g of the expected product were obtained in the form of a white solid by crystallization from iso ether. M.p.=131° C.

Workup

  1. stirringthe reaction medium was stirred for 4 hours at room temperature
  2. concentrationIt was concentrated under vacuum
  3. customto remove the residual THF
  4. extractionIt was then extracted with AcOEt
  5. washwashed with water
  6. dry with materialthe organic phase was dried over sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe residue obtained
  9. customwas then purified by chromatography on silica

Sources & evidence

ORD record
ord-fc6447612f1b4ac39c884794c9c38b1a
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

Loading…