Diethyl Ether → HCID 18957140, compound

HRID 2379476Notes

Reaction equation

HRID 2379476 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C([O-])(=O)C.[Na+].[CH3:17][CH:18]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH:26]([CH3:28])[CH3:27])[C:21]=1[NH:29][C:30](=[O:52])[N:31]([C:38]1[N:39]=[N:40][N:41]([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][OH:51])[N:42]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH3:19].C(OCC)C>ClCCl>[CH3:19][CH:18]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH:26]([CH3:27])[CH3:28])[C:21]=1[NH:29][C:30](=[O:52])[N:31]([C:38]1[N:39]=[N:40][N:41]([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH:50]=[O:51])[N:42]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[CH3:17]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 517045Sodium AcetateHCID 18957142HCID 18957142, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 18957140HCID 18957140, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred, room temperature suspension of pyridinium chlorochromate (0.720 g, 0.00334 mol) and anhydrous sodium acetate (0.0546 g, 0.000666 mol) in dichloromethane (6 mL) was added dropwise over 20 minutes a solution of N'-[2,6-bis(1-methylethyl)-phenyl]-N-[2-(8-hydroxyoctyl)-2H-tetrazol-5-yl]-N-phenyl-urea (1.09 g, 0.00221 mol) in dichloromethane (6 mL), and the mixture was stirred. After 2 hours, diethyl ether (4 mL) was added and the mixture was filtered through celite. The filtercake was washed with dichloromethane. The filtrate and washings were rotoevaporated, and the residue was chromatographed on silica gel (135 g, 230-400 mesh) using PET etherdiethyl ether (1:2, 15-125 mL) as eluent. Fractions containing product were rotoevaporated from dichloromethane to an oil. The oil was dried in vacuo wherein it solidified, yield 0.7108 g (65%) of the title compound, mp=104°-106° C.

Workup

  1. filtrationthe mixture was filtered through celite
  2. washThe filtercake was washed with dichloromethane
  3. customthe residue was chromatographed on silica gel (135 g, 230-400 mesh)
  4. additionFractions containing product
  5. customThe oil was dried in vacuo wherein it

Sources & evidence

ORD record
ord-040d29aa79594e2cab633f092ac1e2f0
Source dataset
uspto-grants-1994_11
Patent number
US05362744

Reaction notes

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