Hydrochloric Acid → 5-{5-[2-Ethyl-3-(2-oxoethyl)phenyl]-1,3-thiazol-2-yl}-2-[(1-methylethyl)oxy]benzonitrile

HRID 1942647Notes

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

Participants

Conditions

Temperature: 75 °C

Procedure

To a mixture of 5-(5-{2-ethyl-3-[(E)-2-(methyloxy)ethenyl]phenyl}-1,3-thiazol-2-yl)-2-[(1-methylethyl)oxy]benzonitrile (D75) (550 mg) in tetrahydrofuran (THF) (20 mL) under nitrogen was added HCl (1.360 mL). The reaction was heated to 75° C. for 6 h. The mixture was concentrated to give the crude product 5-{5-[2-ethyl-3-(2-oxoethyl)phenyl]-1,3-thiazol-2-yl}-2-[(1-methylethyl)oxy]benzonitrile (D76) (531 mg) as a brown oil. MS (ES): C23H22N2O2S requires 390. found 391.0 (M+H+).

Workup

concentrationThe mixture was concentrated

Sources & evidence

ORD record: ord-57e19840f7ea4e16919d54a10cd68b7c
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389508B2

Reaction notes

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