Water → [5-Fluoro-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-(methyloxy)phenyl]acetaldehyde

HRID 1942611Notes

Reaction equation

HRID 1942611 reaction equation
[F:1][C:2]1[CH:3]=[C:4](/[CH:29]=[CH:30]/[O:31]C)[C:5]([O:27][CH3:28])=[C:6]([C:8]2[S:9][C:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH:20]([CH3:22])[CH3:21])=[C:15]([C:23]([F:26])([F:25])[F:24])[CH:14]=3)=[N:11][N:12]=2)[CH:7]=1.[I-].[Na+].C[Si](Cl)(C)C.O>C(#N)C>[F:1][C:2]1[CH:7]=[C:6]([C:8]2[S:9][C:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH:20]([CH3:21])[CH3:22])=[C:15]([C:23]([F:24])([F:25])[F:26])[CH:14]=3)=[N:11][N:12]=2)[C:5]([O:27][CH3:28])=[C:4]([CH2:29][CH:30]=[O:31])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 669818282-{5-fluoro-2-(methyloxy)-3-[(E)-2-(methyloxy)ethenyl]phenyl}-5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazole

Product 1

HCID 86659002[5-Fluoro-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-(methyloxy)phenyl]acetaldehydeYield 103.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-{5-fluoro-2-(methyloxy)-3-[(E)-2-(methyloxy)ethenyl]phenyl}-5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazole (D34) (170 mg) and sodium iodide (109 mg) in acetonitrile (20 mL) stirred under nitrogen at room temperature was added TMSCl (0.093 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-fluoro-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-(methyloxy)phenyl]acetaldehyde (D35) (170 mg) as a yellow oil. MS (ES): C21H18F4N2O3S requires 454. found 455.1 (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-c2ee8a45734946cd9b67b262fdb9ee01
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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