Sodium Hydroxide → HCID 53864123, compound

HRID 1646439Notes

Reaction equation

HRID 1646439 reaction equation
[CH:1]([C:4]1([CH3:23])[C:8](=[O:9])[NH:7][C:6]([C:10]2[C:15]3[S:16][CH:17]=[CH:18][C:14]=3[CH:13]=[CH:12][C:11]=2[C:19]([O:21]C)=[O:20])=[N:5]1)([CH3:3])[CH3:2].[OH-].[Na+]>O1CCCC1>[CH:1]([C:4]1([CH3:23])[C:8](=[O:9])[NH:7][C:6]([C:10]2[C:15]3[S:16][CH:17]=[CH:18][C:14]=3[CH:13]=[CH:12][C:11]=2[C:19]([OH:21])=[O:20])=[N:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54545159HCID 54545159, compound

Product 1

HCID 53864123HCID 53864123, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 7-(4-isopropyl-4methyl-5-oxo-2-imidazolin-2-yl)-6-benzo [b]thiophene carboxylate (90% pure, 0.420 g, 1.20 mmol), aqueous sodium hydroxide (1.01 mL, 2.53 mmol) and tetrahydrofuran (15 mL) is stirred overnight at 40°-45° C., cooled to room temperature, concentrated in vacuo, and acidified to pH 1-2 with concentrated sulfuric acid. Extraction with ethyl acetate, drying (MgSO4), concentration and recrystallization from acetonitrile:hexanes (9:1) affords the title product as an off-white solid, 0.22 g, mp 200°-202° C.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionExtraction with ethyl acetate
  3. customdrying
  4. concentration(MgSO4), concentration and recrystallization from acetonitrile:hexanes (9:1)

Sources & evidence

ORD record
ord-17098dc7ff0944878126e4843e4db581
Source dataset
uspto-grants-1993_01
Patent number
US05180419

Reaction notes

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