Sodium hydride → HCID 22903625, compound

HRID 1489017Notes

Reaction equation

HRID 1489017 reaction equation
F[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH:6]([N:12]1[CH:16]=[CH:15][N:14]=[C:13]1[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:5]2.N1C=CN=C1C(OCC)=O.[H-].[Na+].BrC1CC2C(=CC([Cl:44])=CC=2)C1=O>ClCCl.C(OCC)(=O)C.CN(C)C=O>[Cl:44][C:10]1[CH:9]=[C:8]2[C:4]([CH2:5][CH:6]([N:12]3[CH:16]=[CH:15][N:14]=[C:13]3[C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:7]2=[O:11])=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 549404ethyl 1H-imidazole-2-carboxylateHCID 122065232-Bromo-6-chloro-1-indanoneHCID 22903624HCID 22903624, compound

Product 1

HCID 22903625HCID 22903625, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226138Dichloromethane ethylacetateSolvent

Procedure

The ethyl 1-(6-chloro-1-oxo-1-indanyl)imidazole-2-carboxylate can be prepared as in Example 1 for the preparation of ethyl 1-(5-fluoro-1-oxo-2-indanyl)imidazole-2-carboxylate but starting with 2.5 g of ethyl imidazole-2-carboxylate, 0.7 g of 80% sodium hydride, 5.4 g of 2-bromo-6-chloro-1-indanone and a total of 70 ml of anhydrous dimethylformamide. After silica gel chromatography with a dichloromethane-ethyl acetate mixture (70-30 by volume), 1 g of ethyl 1-(6-chloro-1-oxo-2-indanyl)imidazole-2-carboxylate is obtained which melts at 180° C.

Sources & evidence

ORD record
ord-ddf09661791e42bfb047565e0a785ad2
Source dataset
uspto-grants-1997_10
Patent number
US05677306

Reaction notes

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