Dimethyl Disulfide → HCID 22259322, compound

HRID 1610969Notes

Reaction equation

HRID 1610969 reaction equation
[CH3:1][S:2]SC.C(P(CCCC)CCCC)CCC.[F:18][C:19]([F:53])([F:52])[C:20]1[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[C:28]2[O:29][CH:30]=[C:31]([CH2:33][O:34][C:35]3[CH:40]=[CH:39][C:38]([CH2:41][CH2:42][CH2:43][CH2:44][N:45]4[CH:49]=[CH:48][N:47]=[C:46]4[CH2:50]O)=[CH:37][CH:36]=3)[N:32]=2)=[CH:22][CH:21]=1.[OH-].[Na+]>ClCCl.N1C=CC=CC=1>[CH3:1][S:2][CH2:50][C:46]1[N:45]([CH2:44][CH2:43][CH2:42][CH2:41][C:38]2[CH:39]=[CH:40][C:35]([O:34][CH2:33][C:31]3[N:32]=[C:28](/[CH:27]=[CH:26]/[C:23]4[CH:24]=[CH:25][C:20]([C:19]([F:53])([F:52])[F:18])=[CH:21][CH:22]=4)[O:29][CH:30]=3)=[CH:36][CH:37]=2)[CH:49]=[CH:48][N:47]=1

Participants

7

Reactant 4

HCID 12232Dimethyl DisulfideHCID 13831TributylphosphineHCID 14798Sodium HydroxideHCID 22259311HCID 22259311, compound

Product 1

HCID 22259322HCID 22259322, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Pyridine (0.600 ml), dimethyl disulfide (0.217 ml) and tributylphosphine (0.600 ml) were added to a solution of [1-[4-[4-[[2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazol-4-yl]methoxy]phenyl]butyl]-1H-imidazol-2-yl]methanol (400 mg) in dichloromethane (8 ml) at room temperature, and the mixture was stirred at room temperature for 6 hr. The reaction mixture was combined with 1N aqueous sodium hydroxide solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:1 to ethyl acetate), and recrystallized from ethyl acetate-diethyl ether-hexane to give the titled compound (213 mg) as a colorless crystal powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:1 to ethyl acetate)
  6. customrecrystallized from ethyl acetate-diethyl ether-hexane

Sources & evidence

ORD record
ord-5271864711364529a046a54a073729f6
Source dataset
uspto-grants-2006_01
Patent number
US06984653B2

Reaction notes

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