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

HRID 1942597Notes

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[S:14][C:15]([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)=[N:16][N:17]=1)[CH3:2].Cl.O.O.CC(=O)OCC>O1CCOCC1>[CH2:1]([C:3]1[C:4]([C:13]2[S:14][C:15]([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)=[N:16][N:17]=2)=[CH:5][CH:6]=[CH:7][C:8]=1[CH2:9][CH:10]=[O:11])[CH3:2]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 2-{2-ethyl-3-[(E)-2-(methyloxy)ethenyl]phenyl}-5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazole (D18) (42 mg) in 1,4-dioxane (15 mL) stirred under nitrogen at room temperature was added 6 M HCl/water (15 mL). The reaction mixture was stirred at 20° C. for 5 h. Water was added. EA was used to extracted the aqueous layer for 3 times. The combined organic phases were washed with brine, dried over sodium sulphate and evaporated in vacuo to give the crude product (2-ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}phenyl)acetaldehyde (D19) (40 mg), which was used directly for the next step. MS (ES): C22H21F3N2O2S requires 434. found 435.0 (M+H+).

Workup

extractionto extracted the aqueous layer for 3 times
washThe combined organic phases were washed with brine
dry with materialdried over sodium sulphate
customevaporated in vacuo

Sources & evidence

ORD record: ord-1b931316b869498889c35d83e9662fd7
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389508B2

Reaction notes

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