Ethyl 3-ethoxy-3-iminopropionate hydrochloride → 2,3,4-trifluoro-N-[1-ethoxy-2-(ethoxycarbonyl)ethylidene]aniline

HRID 344892

Reaction equation

[F:1][C:2]1[C:8]([F:9])=[C:7]([F:10])[CH:6]=[CH:5][C:3]=1[NH2:4].Cl.[CH2:12]([O:14][C:15]([CH2:17][C:18](=N)[O:19][CH2:20][CH3:21])=[O:16])[CH3:13]>C(O)C>[F:1][C:2]1[C:8]([F:9])=[C:7]([F:10])[CH:6]=[CH:5][C:3]=1[N:4]=[C:18]([O:19][CH2:20][CH3:21])[CH2:17][C:15]([O:14][CH2:12][CH3:13])=[O:16]

Participants

Conditions

Temperature: 20 °C

Procedure

2,3,4-Trifluoroaniline (58.8 g) is added in a single portion with stirring to a solution of 2-ethoxycarbonyl-1-ethoxyethylideneamine hydrochloride (90 g) in ethanol (820 cc). After 48 hours' stirring at a temperature in the region of 20° C., the suspension obtained is filtered; the filtrate is concentrated under reduced pressure (20 kPa) at a temperature in the region of 50° C. The oily residue is taken up with water (250 cc). The mixture obtained is extracted with ethyl ether (3×200 cc). The combined organic extracts are washed with water (4×150 cc), dried over magnesium sulphate and concentrated under reduced pressure (20 kPa) at approximately 30° C. 2,3,4-Trifluoro-N-[1-ethoxy-2-(ethoxycarbonyl)ethylidene]aniline (122 g) is obtained in the form of a yellow oil, which is used without further purification for the subsequent steps.

Workup

customthe suspension obtained
filtrationis filtered
concentrationthe filtrate is concentrated under reduced pressure (20 kPa) at a temperature in the region of 50° C
customThe mixture obtained
extractionis extracted with ethyl ether (3×200 cc)
washThe combined organic extracts are washed with water (4×150 cc)
dry with materialdried over magnesium sulphate
concentrationconcentrated under reduced pressure (20 kPa) at approximately 30° C

Sources & evidence

ORD record: ord-9c008d3139064a119e4be92090e7f59b
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05053509

Linked notes

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