Hydrochloric Acid → HCID 58494132, compound

HRID 1942634Notes

Reaction equation

HRID 1942634 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[N:17]=[C:16]([C:18]2[CH:19]=[CH:20][C:21]([CH2:26][CH:27]([CH3:29])[CH3:28])=[C:22]([CH:25]=2)[C:23]#[N:24])[S:15][N: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[N:17]=[C:16]([C:18]2[CH:19]=[CH:20][C:21]([CH2:26][CH:27]([CH3:28])[CH3:29])=[C:22]([CH:25]=2)[C:23]#[N:24])[S:15][N:14]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66981904HCID 66981904, compound

Product 1

HCID 58494132HCID 58494132, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 5-(3-{2-ethyl-3-[(E)-2-(methyloxy)ethenyl]phenyl}-1,2,4-thiadiazol-5-yl)-2-(2-methylpropyl)benzonitrile (D61) (500 mg) in tetrahydrofuran (THF) (20 mL) stirred under nitrogen at room temperature was added 2M hydrochloric acid (1.239 mL). The reaction mixture was stirred at 70° C. for 2 h. After cooling the reaction, the solution was condensed under reduced pressure to give 5-{3-[2-ethyl-3-(2-oxoethyl)phenyl]-1,2,4-thiadiazol-5-yl}-2-(2-methylpropyl)benzonitrile (D62) (483 mg), which was used directly in the next step without further purification. MS (ES): C23H23N3OS requires 389. found 390.1 (M+H+).

Workup

  1. temperatureAfter cooling
  2. customthe reaction
  3. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-469412f3ad4d4d88b54849db639b7f59
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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