1,2-Dibromoethane → HCID 14150220, compound

HRID 648793Notes

Reaction equation

HRID 648793 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][CH2:27]Br>CN(C)C=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]([C:12]2([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:27][CH2:26]2)=[O:18])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 12741176Ethyl 3-(4-nitroanilino)-3-oxopropanoate

Product 1

HCID 14150220HCID 14150220, compoundYield 15%

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 (39.6 mmol) of ethyl 3-[(4-nitrophenyl)amino]-3-oxopropanoate, 13.7 grams (99.1 mmol) of anhydrous potassium carbonate, 40 milliliters of anhydrous dimethylformamide and 3.4 milliliters (40.0 mmol) of 1,2-dibromoethane were reacted for a period of 7 days to give 1.6 grams (5.8 mmol) of ethyl 1-(4-nitrophenylaminocarbonyl)cyclopropanecarboxylate as a pale yellow solid having a melting point of 159.0° C.-161.0° C. The total yield was 15 percent. Recrystallization from methylene chloride-hexane furnished 1.39 grams (5.0 mmol) of 1-(4-nitrophenylaminocarbonyl)cyclopropanecarboxylate as pale yellow needles having a melting point of 159.5° C.-161.0° C. NMR analysis of the product indicated the following:

Sources & evidence

ORD record
ord-e34acf13b1d04a4184aa9bc3a8e15847
Source dataset
uspto-grants-1988_04
Patent number
US04736056

Reaction notes

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