Hydrate;hydrochloride → HCID 58494137, compound

HRID 1942593Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:13][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:15][N:16]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].Cl.O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:13][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:15][N:16]=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 2-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-5-{2-ethyl-3-[(E)-2-(methyloxy)ethenyl]phenyl}-1,3,4-thiadiazole (D14) (100 mg) in tetrahydrofuran (THF) (15 mL) stirred under nitrogen at room temperature was added 2M HCl/water (0.3 mL). The reaction mixture was stirred at 70° C. for 4 h. The reaction mixture was concentrated to afford the crude product [3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-2-ethylphenyl]acetaldehyde (D15) (97 mg). MS (ES): C21H21ClN2O2S requires 400. found 401.1 (M+H+).

Workup

concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record: ord-acb9836fa08148b8882e53953c307f35
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389508B2

Reaction notes

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