Hydrochloric Acid → HCID 178527930, compound

HRID 1921699Notes

Reaction equation

HRID 1921699 reaction equation
[OH-].[Li+].[Br:3][C:4]1[N:5]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]([CH:27]3[CH2:29][CH2:28]3)=[CH:19][CH:18]=2)[C:6]([S:9]CCC(OCC)=O)=[N:7][N:8]=1.Cl>C1COCC1.CO>[Br:3][C:4]1[N:5]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]([CH:27]3[CH2:29][CH2:28]3)=[CH:19][CH:18]=2)[C:6]([SH:9])=[N:7][N:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 46178847ethyl 3-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)propanoate

Product 1

HCID 178527930HCID 178527930, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous lithium hydroxide solution (1M, 437 μL, 0.437 mmol, 3 eq.) was added to a solution of ethyl 3-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)propanoate (65 mg, 0.146 mmol) in THF (1.5 mL) and methanol (1 mL). The mixture was stirred at room temperature for ˜2 hours, and HCl (1N, 584 μL, 0.584 mmol, 4 eq.) added. The mixture was concentrated, a little water added, sonicated and the off-white solids isolated by filtration. The isolated material was placed into small amount of methanol, sonicated again, and then filtered to give 5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-thiol as an off-white solid (39 mg, 78%).

Workup

  1. concentrationThe mixture was concentrated
  2. additiona little water added
  3. customsonicated
  4. customthe off-white solids isolated by filtration
  5. customsonicated again
  6. filtrationfiltered

Sources & evidence

ORD record
ord-e0fb575af178416792ca92658b202169
Source dataset
uspto-grants-2012_05
Patent number
US08173690B2

Reaction notes

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