1,2-Dibromoethane → HCID 14150219, compound

HRID 648792Notes

Reaction equation

HRID 648792 reaction equation
[C:1]([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)#[N:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26]Br>CN(C)C=O>[C:1]([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)#[N:2]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 20145882HCID 20145882, compound

Product 1

HCID 14150219HCID 14150219, compoundYield 47%

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 (43.0 mmol) of ethyl 3-[(4-cyanophenyl)amino]-3-oxopropanoate, 14.8 grams (108.0 mmol) of anhydrous potassium carbonate, 40 milliliters of anhydrous dimethylformamide and 3.7 milliliters (43.0 mmol) of 1,2-dibromoethane were reacted for a period of 8 days to give 5.19 grams (20.0 mmol) of ethyl 1-(4-cyanophenylaminocarbonyl)cyclopropanecarboxylate as a colorless solid having a melting point of 132.0° C.-133.5° C. The total yield was 47 percent. An analytical sample was prepared by recrystallization from hexane-ethyl acetate having a melting point of 133.0° C.-134.0° C. NMR analysis of the product indicated the following:

Sources & evidence

ORD record
ord-1a5691dfceda44549b1689cb1589d07f
Source dataset
uspto-grants-1988_04
Patent number
US04736056

Reaction notes

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