Sodium Iodide → HCID 58494089, compound

HRID 1942672Notes

Reaction equation

HRID 1942672 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[O:27][CH3:28])[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>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]([O:27][CH3:28])=[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]([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 584941155-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-3-{2-(methyloxy)-3-[(E)-2-(methyloxy)ethenyl]phenyl}-1,2,4-thiadiazole

Product 1

HCID 58494089HCID 58494089, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-3-{2-(methyloxy)-3-[(E)-2-(methyloxy)ethenyl]phenyl}-1,2,4-thiadiazole (D102) (152 mg, 0.365 mmol) and sodium iodide (109 mg, 0.729 mmol) in Acetonitrile (10 mL) was added TMSCl (0.093 mL, 0.729 mmol) dropwise. The reaction mixture was stirred at room temperature overnight (16 h). The reaction was quenched with water (10 mL). Then EA (10 mL) was added to the reaction mixture. The organic phase was separated. The aqueous phase was extracted with EA (10 mL×2). The combined organic layers was dried over anhydrous sodium sulphate. After filtration and concentration, the residue was purified by column chromatography (EA/Hexane: 0 to 50%) to afford [3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazol-3-yl)-2-(methyloxy)phenyl]acetaldehyde (D103) (87.6 mg). MS (ES): C20H19ClN2O3S requires 402.1. found 403.1 (M+H+).

Workup

  1. customThe reaction was quenched with water (10 mL)
  2. additionThen EA (10 mL) was added to the reaction mixture
  3. customThe organic phase was separated
  4. extractionThe aqueous phase was extracted with EA (10 mL×2)
  5. dry with materialThe combined organic layers was dried over anhydrous sodium sulphate
  6. filtrationAfter filtration and concentration
  7. customthe residue was purified by column chromatography (EA/Hexane: 0 to 50%)

Sources & evidence

ORD record
ord-4a121607b8b041728817b899eb5b6728
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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