1,2-Dibromoethane → HCID 14150221, compound

HRID 648799Notes

Reaction equation

HRID 648799 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26]Br>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([C:11]1([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:26][CH2:25]1)=[O:17]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 12741175N-(2,4-Dichlorophenyl)-3-ethoxy-3-oxopropanimidic acid

Product 1

HCID 14150221HCID 14150221, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a manner similar to the procedure described in Example B except that a one liter three-necked Morton flask was used, 39.0 grams (0.14 mol) of ethyl 3-[(2,4-dichlorophenyl)amino]-3-oxopropanoate, 53.9 grams (0.39 mol) of anhydrous potassium carbonate, 125 milliliters of anhydrous dimethylformamide and 13.4 milliliters (0.16 mol) of 1,2-dibromoethane were reacted for a period of 65 hours to give 35.3 grams (0.117 mol) of ethyl 1-(2,4-dichlorophenylaminocarbonyl)cyclopropanecarboxylate as a pale yellow solid having a melting point of 95.0° C.-96.0° C. The total yield was 83 percent. NMR analysis of the product indicated the following:

Sources & evidence

ORD record
ord-5f29f9f5c036478298e674657789e0f1
Source dataset
uspto-grants-1988_04
Patent number
US04736056

Reaction notes

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