Water → HCID 58494176, compound

HRID 1942674Notes

Reaction equation

HRID 1942674 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][N:15]=[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:13]=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:16][N:15]=[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:13]=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 584941665-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-3-{2-methyl-3-[(E)-2-(methyloxy)ethenyl]phenyl}-1,2,4-thiadiazole

Product 1

HCID 58494176HCID 58494176, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-3-{2-methyl-3-[(E)-2-(methyloxy)ethenyl]phenyl}-1,2,4-thiadiazole (D105) (130 mg, 0.324 mmol) and sodium iodide (97 mg, 0.649 mmol) in Acetonitrile (8 mL) stirred under nitrogen at room temperature was added TMSCl (0.083 mL, 0.649 mmol) dropwise. The reaction mixture was stirred at room temperature for 1 hr. Water was added. The aqeuous 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 [3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazol-3-yl)-2-methylphenyl]acetaldehyde (D106) (120 mg) as a yellow oil, which was used for the next step without further purification. MS (ES): C20H19ClN2O2S requires 386.1. found 387.2 (M+H+).

Workup

  1. extractionThe aqeuous 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-a70492cda0e742ec88e33ec34d99f299
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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