Sodium hydride → 3-isopropyl-3-methyl-3H-imidazo[2,1-a]isoindole-2,5-dione

HRID 328368Notes

Reaction equation

HRID 328368 reaction equation
[H-].[Na+].[CH:3]([C:6]([CH3:21])([N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=O)[C:7]([NH2:9])=[O:8])([CH3:5])[CH3:4]>>[CH:3]([C:6]1([CH3:21])[N:10]2[C:18](=[O:19])[C:17]3[C:12]([C:11]2=[N:9][C:7]1=[O:8])=[CH:13][CH:14]=[CH:15][CH:16]=3)([CH3:5])[CH3:4]

Participants

3

Reactant 2

HCID 24758Sodium hydrideHCID 4916589alpha-Isopropyl-alpha-methyl-1,3-dioxo-2-isoindolineacetamide

Product 1

HCID 27292473-isopropyl-3-methyl-3H-imidazo[2,1-a]isoindole-2,5-dione

Procedure

Following the procedure described in Example 1 and sodium hydride as the base, but substituting (+)-α-isopropyl-α-methyl-1,3-dioxo-2-isoindoleacetamide for the racemic compound, the product (-)-3-isopropyl-3-methyl-5H-imidazo[2,1-a]isoindole-2(3H),5-dione is obtained, melting point 137.5°-139° C, [α]D25 -64.74° (THF, C 0.097).

Sources & evidence

ORD record
ord-e6f258938da347488926c6d7139326c4
Source dataset
uspto-grants-1977_04
Patent number
US04017510

Reaction notes

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