Triethylamine → ethyl 2-(4-methoxyanilino)-4-oxofuran-3-carboxylate

HRID 402593Notes

Reaction equation

HRID 402593 reaction equation
Cl[CH2:2][C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]=[C:20]=[O:21])=[CH:15][CH:14]=1.C(N(CC)CC)C>C(OCC)C.C(OCC)(=O)C>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[O:21][CH2:2][C:3](=[O:10])[C:4]=2[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69484Ethyl 4-chloroacetoacetateHCID 794431-Isocyanato-4-methoxybenzene

Product 1

HCID 2822533ethyl 2-(4-methoxyanilino)-4-oxofuran-3-carboxylate

Reagents, catalysts & solvents 1

HCID 21584169Diethylether ethylacetateSolvent

Procedure

Under a nitrogen atmosphere, to a mixed solution of ethyl 4-chloroacetoacetate (0.82 mL, 6.0 mmol) and 4-methoxyphenyl isocyanate 1.1 g, 7.2 mmol) in diethyl ether/ethyl acetate (10 mL/1.0 mL) that cooled with ice bath, triethylamine (0.96 mL, 6.9 mmol) was added dropwise. The reaction mixture was stirred at ambient temperature for 1.5 h then the precipitate was collected by filtration, washed with diethyl ether, 1M hydrochloric acid solution, water and diethyl ether, and then dried to afford ethyl 2-[(4-methoxyphenyl)amino]-4-oxo-4,5-dihydrofuran-3-carboxylate as solid (1.3 g, y. 78%).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with diethyl ether, 1M hydrochloric acid solution, water and diethyl ether
  3. customdried

Sources & evidence

ORD record
ord-027e28158d4e4b4d9793f0b3b60dd5a4
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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