Ethyl 4-chloroacetoacetate → Ethyl 2-[[4-(ethoxycarbonyl)phenyl]amino]4,5-dihydro-4-oxo-3-furancarboxylate

HRID 231125Notes

Reaction equation

HRID 231125 reaction equation
Cl[CH2:2][C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[N:11]([C:14]1[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=1)=[C:12]=[O:13]>C(N(CC)CC)C>[CH2:21]([O:20][C:18]([C:17]1[CH:23]=[CH:24][C:14]([NH:11][C:12]2[O:13][CH2:2][C:3](=[O:10])[C:4]=2[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:15][CH:16]=1)=[O:19])[CH3:22]

Participants

4

Reactant 2

HCID 69484Ethyl 4-chloroacetoacetateHCID 589805Ethyl 4-isocyanatobenzoate

Product 1

HCID 14198527Ethyl 2-[[4-(ethoxycarbonyl)phenyl]amino]4,5-dihydro-4-oxo-3-furancarboxylate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Triethylamine (9.87 ml) was added dropwise, over a period of 1 hour to a cooled (ice bath) solution of ethyl 4-chloroacetoacetate (9.87 g, 60 mmol) and ethyl p-isocyanatobenzoate (14.34 g, 75 mmol) in 60 ml of petroleum ether-ethyl acetate (10:1 by volume), under nitrogen atmosphere. The reaction mixture was stirred at 0°-5° C. for 1 hour. The resulting ethyl 2-[[4-(ethoxycarbonyl)phenyl]-amino]-4,5-dihydro-4-oxo-3-furancarboxylate was filtered and then washed sequentially with petroleum ether, 1 N hydrochloric acid and water. Yield 13.0 g Mp 152°-153° C. (isopropanol).

Workup

  1. filtrationThe resulting ethyl 2-[[4-(ethoxycarbonyl)phenyl]-amino]-4,5-dihydro-4-oxo-3-furancarboxylate was filtered
  2. washwashed sequentially with petroleum ether, 1 N hydrochloric acid and water

Sources & evidence

ORD record
ord-e9bcb238e0b247768e6bd2b4ecf5655d
Source dataset
uspto-grants-1989_07
Patent number
US04845122

Reaction notes

Loading…