Water → HCID 86659001, compound

HRID 1942607Notes

Reaction equation

HRID 1942607 reaction equation
[CH2:1]([C:3]1[C:8](/[CH:9]=[CH:10]/[O:11]C)=[CH:7][CH:6]=[CH:5][C:4]=1[C:13]1[S:17][C:16]([C:18]2[CH:19]=[CH:20][C:21]([CH2:26][CH:27]([CH3:29])[CH3:28])=[C:22]([CH:25]=2)[C:23]#[N:24])=[N:15][N:14]=1)[CH3:2].[I-].[Na+].C[Si](Cl)(C)C.O>C(#N)C>[CH2:1]([C:3]1[C:8]([CH2:9][CH:10]=[O:11])=[CH:7][CH:6]=[CH:5][C:4]=1[C:13]1[S:17][C:16]([C:18]2[CH:19]=[CH:20][C:21]([CH2:26][CH:27]([CH3:28])[CH3:29])=[C:22]([CH:25]=2)[C:23]#[N:24])=[N:15][N:14]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 66981731HCID 66981731, compound

Product 1

HCID 86659001HCID 86659001, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-(5-{2-ethyl-3-[(E)-2-(methyloxy)ethenyl]phenyl}-1,3,4-thiadiazol-2-yl)-2-(2-methylpropyl)benzonitrile (D30) (120 mg) and sodium iodide (89 mg) in acetonitrile (20 mL) stirred under nitrogen at room temperature was added TMSCl (0.076 mL) dropwise. The reaction mixture was stirred at room temperature for 10 min. Water was added. The aqueous solution was extracted with EA for 3 times. The organic phase was washed with saturated Na2S2O3 solution and saturated brine, dried over sodium sulphate and evaporated in vacuo to afford the crude product 5-{5-[2-ethyl-3-(2-oxoethyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-(2-methylpropyl)benzonitrile (D31) (104 mg) as a yellow oil. MS (ES): C23H23N3OS requires 389. found 390.1 (M+H+).

Workup

  1. extractionThe aqueous solution was extracted with EA for 3 times
  2. washThe organic phase was washed with saturated Na2S2O3 solution and saturated brine
  3. dry with materialdried over sodium sulphate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-f6a9897bc86f428393e6a570c05c8982
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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