Lithium Hydroxide → HCID 90404220, compound

HRID 1772459Notes

Reaction equation

HRID 1772459 reaction equation
[C:1](/[C:3](=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:20]=[CH:19][N:18]([C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=3)[N:17]=2)=[CH:12][CH:11]=1)/[C:4]([O:6]CC)=[O:5])#[N:2].[OH-].[Li+]>O1CCCC1.CO.O>[C:1](/[C:3](=[CH:9]/[C:10]1[CH:11]=[CH:12][C:13]([C:16]2[N:20]=[CH:19][N:18]([C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]([F:29])([F:30])[F:31])=[CH:23][CH:22]=3)[N:17]=2)=[CH:14][CH:15]=1)/[C:4]([OH:6])=[O:5])#[N:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 90438206HCID 90438206, compound

Product 1

HCID 90404220HCID 90404220, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To (Z)-ethyl 2-cyano-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acrylate (C46) (2.5 g, 5.8 mmol) in tetrahydrofuran/methanol/water (3:2:1, 42 mL) was added lithium hydroxide (2.5 mL, 7.5 mmol) and stirred at room temperature for 18 hours. The reaction mixture was concentrated under vacuum, cooled in an ice bath, and acidified with hydrogen chloride (2 N). The precipitate was filtered and washed with cold water to afford the title compound as a brown solid (2.2 g, 82%): 1H NMR (400 MHz, DMSO-d6) δ 9.49 (s, 1H), 8.39 (s, 1H), 8.28 (d, J=8.5 Hz, 2H), 8.18 (d, J=8.5 Hz, 2H), 8.13-8.08 (m, 2H), 7.64 (d, J=8.4 Hz, 2H); ESIMS m/z 401 ([M+H]+).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. temperaturecooled in an ice bath
  3. filtrationThe precipitate was filtered
  4. washwashed with cold water

Sources & evidence

ORD record
ord-9c44e313498540659979bbc4617a14ff
Source dataset
uspto-grants-2016_02
Patent number
US09249133B2

Reaction notes

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