Sodium Bisulfate → HCID 53386233, compound

HRID 1893181Notes

Reaction equation

HRID 1893181 reaction equation
CO[CH2:3][O:4][C:5]1[CH:6]=[C:7]([C:15]2[N:19]=[CH:18][N:17](/[CH:20]=[CH:21]\[C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23])[N:16]=2)[CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1.OS([O-])(=O)=O.[Na+].[C:34]([O:37][CH2:38][CH3:39])(=[O:36])[CH3:35].[CH3:40]CCCCC>C(Cl)Cl>[CH:25]([O:24][C:22](=[O:23])/[CH:21]=[CH:20]\[N:17]1[CH:18]=[N:19][C:15]([C:7]2[CH:6]=[C:5]([CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=2)[O:4]/[CH:3]=[CH:35]/[C:34]([O:37][CH:38]([CH3:40])[CH3:39])=[O:36])=[N:16]1)([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 516919Sodium BisulfateHCID 21226206Ethyl acetate hexaneHCID 66996132HCID 66996132, compound

Product 1

HCID 53386233HCID 53386233, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 3-neck 50 mL RBF, (Z)-isopropyl 3-(3-(3-(methoxymethoxy)-5-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)acrylate (0.05 g, 1 eq.) was dissolved in DCM (5 mL) and activated NaHSO4.SiO2 (0.050 g) was added and reaction mixture was stirred at RT for 30 min. Reaction completion was monitored on TLC using ethyl acetate:hexane (3:7) mobile phase. Reaction mixture was filtered and concentrates under reduced pressure to afford 0.02 g of pure compound, Yield (45%). 1H NMR (400 MHz, CDCl3): δ 10.5 (s, 1H, D2O Exchangeable), 9.14 (s, 1H), 7.703-7.707 (d, 2H), 7.45-7.48 (d, J=10 Hz, 1H), 7.14 (s, 1H), 5.973-5.998 (d, J=10 Hz, 1H), 5.02-5.08 (m, 1H), δ 1.22-1.24 (s, 6H): LCMS for C15H14F3N3O3 MW 341.3 found 341.8 at 3.812 min (LCMS 98.66%).

Workup

  1. customreaction mixture
  2. customReaction completion
  3. customReaction mixture
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-d9e9fbbcced04cea983376f160c4f31d
Source dataset
uspto-grants-2013_08
Patent number
US08513230B2

Reaction notes

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