Hydrochloric Acid → HCID 58494135, compound

HRID 1942678Notes

Reaction equation

[Cl:1][C:2]1[C:3]([O:25][CH:26]([CH3:28])[CH3:27])=[N:4][CH:5]=[C:6]([C:8]2[S:12][N:11]=[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15](/[CH:19]=[CH:20]/[O:21]C)[C:14]=3[CH2:23][CH3:24])[N:9]=2)[CH:7]=1.Cl>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[S:12][N:11]=[C:10]([C:13]3[C:14]([CH2:23][CH3:24])=[C:15]([CH2:19][CH:20]=[O:21])[CH:16]=[CH:17][CH:18]=3)[N:9]=2)[CH:5]=[N:4][C:3]=1[O:25][CH:26]([CH3:28])[CH3:27]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 3-chloro-5-(3-{2-ethyl-3-[(E)-2-(methyloxy)ethenyl]phenyl}-1,2,4-thiadiazol-5-yl)-2-[(1-methylethyl)oxy]pyridine (D110) (2 g, 4.81 mmol) in Tetrahydrofuran (50 mL) was added HCl (4.81 mL, 9.62 mmol). The resulted solution was heated to 70° C. for 2 h. THF was removed in vacuo to afford [3-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-thiadiazol-3-yl)-2-ethylphenyl]acetaldehyde (D111) (2 g, 4.98 mmol, 103% yield) as a crude product, which was used directly without further purification. MS (ES): C20H20ClN3O2S requires 401.0. found 402.0 (M+H+).

Workup

customTHF was removed in vacuo

Sources & evidence

ORD record: ord-ae1d7023b4314fda8b7308491c33e578
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389508B2

Reaction notes

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