HCID 58494117, compound → [3-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazol-3-yl)-2-ethylphenyl]acetaldehyde

HRID 1942625Notes

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[CH2:27][CH3:28])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]>O1CCCC1.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][N:15]=[C:14]([C:17]3[C:18]([CH2:27][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]([CH3:11])[CH3:10]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-3-{2-ethyl-3-[(E)-2-(methyloxy)ethenyl]phenyl}-1,2,4-thiadiazole (D51) (313 mg) in tetrahydrofuran (THF) (20 mL) stirred under nitrogen at room temperature was added 14 drops 2M hydrochloric acid. The reaction mixture was stirred at 70° C. for 4 h. After cooling the reaction, the solution was condensed under reduced pressure to give [3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazol-3-yl)-2-ethylphenyl]acetaldehyde (D52) (300 mg), which was used directly in the next step without further purification. MS (ES): C21H21 ClN2O2S requires 400. found 401.1 (M+H+).

Workup

temperatureAfter cooling
customthe reaction
customcondensed under reduced pressure

Sources & evidence

ORD record: ord-8e26bfa5ea364822831f2b82755d3cb2
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389508B2

Reaction notes

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