Water → HCID 58494069, compound

HRID 1942666Notes

Reaction equation

HRID 1942666 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19](/[CH:23]=[CH:24]/[O:25]C)[C:18]=3[CH3:27])=[N:15][N:16]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[I-].[Na+].C[Si](Cl)(C)C.O>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:13][C:14]([C:17]3[C:18]([CH3:27])=[C:19]([CH2:23][CH:24]=[O:25])[CH:20]=[CH:21][CH:22]=3)=[N:15][N:16]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 58494072HCID 58494072, compound

Product 1

HCID 58494069HCID 58494069, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-5-{2-methyl-3-[(E)-2-(methyloxy)ethenyl]phenyl}-1,3,4-thiadiazole (D96) (690 mg, 1.721 mmol) and sodium iodide (516 mg, 3.44 mmol) in Acetonitrile (20 mL) stirred under nitrogen at room temperature was added TMSCl (0.440 mL, 3.44 mmol) 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 [3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-2-methylphenyl]acetaldehyde (D97) (666 mg) as a yellow oil, which was used for the next step without further purification. MS (ES): C20H19ClN2O2S requires 386.0. found 387.0 (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-d04f3c028f504020b3e12c58e138125f
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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