1,2-Dibromoethane → HCID 14150217, compound

HRID 648791Notes

Reaction equation

HRID 648791 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26]Br>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]([C:11]2([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:26][CH2:25]2)=[O:17])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 12324961Ethyl 3-(4-methoxyanilino)-3-oxopropanoate

Product 1

HCID 14150217HCID 14150217, compoundYield 52,381%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a manner similar to the procedure described in Example B except that a 100 milliliter three-necked Morton flask was used, 10.0 grams (42.0 mmol) of ethyl 3-[(4-methoxyphenyl)amino]-3-oxopropanoate, 14.54 grams (105.0 mmol) of anhydrous potassium carbonate, 30 milliliters of dimethylformamide and 7.9 grams (42.0 mmol) of 1,2-dibromoethane were reacted for a period of 12 days to give 5.74 grams (22.0 mol) of ethyl 1-(4-methoxyphenylaminocarbonyl)cyclopropanecarboxylate as a colorless solid having a melting point of 89.5° C.-91.0° C. The total yield was 56 percent. NMR analysis of the product indicated the following:

Sources & evidence

ORD record
ord-210ccfed87574a0bb7fb37a104481308
Source dataset
uspto-grants-1988_04
Patent number
US04736056

Reaction notes

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