Methane, tris(methylthio)- → HCID 178504086, compound

HRID 1433209Notes

Reaction equation

HRID 1433209 reaction equation
[CH3:1][S:2][CH:3]([S:6][CH3:7])[S:4][CH3:5].C([Li])CCC.[F:13][C:14]([F:41])([F:40])[C:15]1[CH:39]=[CH:38][C:18]([O:19][CH2:20][C:21]2[NH:25][C:24]3[CH:26]=[CH:27][C:28]([C:30]4[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=4[CH:32]=[O:33])=[CH:29][C:23]=3[N:22]=2)=[CH:17][CH:16]=1>C1COCC1>[CH3:1][S:2][C:3]([S:6][CH3:7])([S:4][CH3:5])[CH:32]([C:31]1[CH:34]=[CH:35][CH:36]=[CH:37][C:30]=1[C:28]1[CH:27]=[CH:26][C:24]2[NH:25][C:21]([CH2:20][O:19][C:18]3[CH:38]=[CH:39][C:15]([C:14]([F:41])([F:40])[F:13])=[CH:16][CH:17]=3)=[N:22][C:23]=2[CH:29]=1)[OH:33]

Participants

5

Reactant 3

HCID 138491Methane, tris(methylthio)-HCID 178418339ButyllithiumHCID 1785194642-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzaldehyde

Product 1

HCID 178504086HCID 178504086, compoundYield 219.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tris(methylthio)methane (0.640 g, 4.15 mmol) in THF (12 mL) at −78° C. was added n-butyllithium (1.6 mL, 4.15 mmol). After stirring for 30 min, 2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzaldehyde (0.274 g, 0.691 mmol, Example 9, Step A) in THF (2 mL) was carefully added to the reaction mixture at −78° C. After 20 min, the reaction was quenched by addition of methanol. The reaction mixture was purified by chromatography (silica, hexanes: EtOAc, 2:1) to afford the title compound as a yellow oil (0.836 g, 94%).

Workup

  1. waitAfter 20 min
  2. customthe reaction was quenched by addition of methanol
  3. customThe reaction mixture was purified by chromatography (silica, hexanes: EtOAc, 2:1)

Sources & evidence

ORD record
ord-3217b77b7e4e4a129a1db2e772feba0e
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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