Sulfuric Acid → HCID 22402930, compound

HRID 439729Notes

Reaction equation

HRID 439729 reaction equation
[CH:1]([C:4]1([CH3:25])[C:8](=[O:9])[NH:7][C:6]([C:10]2[C:18]([C:19]([O:21]C)=[O:20])=[CH:17][CH:16]=[C:15]3[C:11]=2[C:12]([CH3:24])=[N:13][N:14]3[CH3:23])=[N:5]1)([CH3:3])[CH3:2].[OH-].[Na+].S(=O)(=O)(O)O>O1CCCC1>[CH:1]([C:4]1([CH3:25])[C:8](=[O:9])[NH:7][C:6]([C:10]2[C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=[C:15]3[C:11]=2[C:12]([CH3:24])=[N:13][N:14]3[CH3:23])=[N:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 54498860HCID 54498860, compound

Product 1

HCID 22402930HCID 22402930, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-1,3-dimethyl-1H-indazole-5-carboxylate (0.310 g, 0.905 mmol), 2N sodium hydroxide (0.91 mL, 1.82 mmol) and tetrahydrofuran (11 mL) is stirred for 1.5 hours at 42°-52° C., cooled in an ice bath, acidified to pH 3-3.5 with 5N sulfuric acid and extracted with chloroform. The organic extract is dried (Na2SO4) and concentrated in vacuo to give a residue which is recrystallized from acetonitrile to afford the title product as a white solid (0.160 g, 53.2%), mp 156.5°-166° C.

Workup

  1. temperaturecooled in an ice bath
  2. extractionextracted with chloroform
  3. extractionThe organic extract
  4. dry with materialis dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto give a residue which
  7. customis recrystallized from acetonitrile

Sources & evidence

ORD record
ord-10d05d7a0f0d4e6a8cd0da56fa7b44c9
Source dataset
uspto-grants-1996_05
Patent number
US05516751

Reaction notes

Loading…