Hydrochloric Acid → 4-((1-Methyl-3,5-dioxo-1,2,4-triazolidin-4-yl)methyl)benzoic acid

HRID 1180113Notes

Reaction equation

HRID 1180113 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[N:5]([CH2:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=2)[C:4](=[O:19])[NH:3]1.[OH-].[Li+].Cl>CO>[CH3:1][N:2]1[C:6](=[O:7])[N:5]([CH2:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=2)[C:4](=[O:19])[NH:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58978277Methyl 4-((1-methyl-3,5-dioxo-1,2,4-triazolidin4-yl)methyl)benzoate

Product 1

HCID 589783024-((1-Methyl-3,5-dioxo-1,2,4-triazolidin-4-yl)methyl)benzoic acidYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Example Z (1.0 g, 0.0038 mol) and lithium hydroxide (0.950 g) in MeOH (10 mL) was stirred at RT for overnight. The mixture was acidified by 2N HCl to pH=5-6 and extracted by CH2Cl2 (3×50 mL). The combined organic layers were washed with H2O, dried (MgSO4) and concentrated in vacuo to yield 4-((1-methyl-3,5-dioxo-1,2,4-triazolidin-4-yl)methyl)benzoic acid (0.6 g, 64%). 1H NMR (CDCl3): 7.71 (d, J=8.4 Hz, 2H), 7.17 (d, J=8.4 Hz, 2H), 4.68 (s, 2H), 2.90 (s, 3H), 2.6 (s, 3H); MS (ESI) m/e: 249 (M+1).

Workup

  1. extractionextracted by CH2Cl2 (3×50 mL)
  2. washThe combined organic layers were washed with H2O
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c6af4177919d47d2bcc028239b6467d4
Source dataset
uspto-grants-2007_10
Patent number
US07279576B2

Reaction notes

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