Hydrochloric Acid → HCID 57522814, compound

HRID 1942623Notes

Reaction equation

HRID 1942623 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[N:17]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[C:20]([C:28]([F:31])([F:30])[F:29])[CH:19]=2)[S:15][N:14]=1)[CH3:2].Cl>O1CCCC1>[CH2:1]([C:3]1[C:4]([C:13]2[N:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[C:20]([C:28]([F:30])([F:29])[F:31])[CH:19]=3)[S:15][N:14]=2)=[CH:5][CH:6]=[CH:7][C:8]=1[CH2:9][CH:10]=[O:11])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57522813HCID 57522813, compound

Product 1

HCID 57522814HCID 57522814, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3-{2-ethyl-3-[(E)-2-(methyloxy)ethenyl]phenyl}-5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,2,4-thiadiazole (D49) (140 mg) in tetrahydrofuran (THF) (10 mL) stirred under nitrogen at room temperature was added hydrochloric acid (0.2 mL). The reaction mixture was stirred at 70° C. for 5 h. After cooling the reaction, the solution was condensed under reduced pressure to give (2-ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,2,4-thiadiazol-3-yl}phenyl)acetaldehyde (D50) (108 mg) as a colorless oil, which was used directly in the next step without further purification. MS (ES): C22H21F3N2O2S requires 434. found 435.2 (M+H+).

Workup

  1. temperatureAfter cooling
  2. customthe reaction
  3. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-8289b8e811b345eb83396e2ce4696cf5
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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