Water → Ethyl 2-[3-(2-fluorophenyl)-1-(3-chloropropyl)ureido]isobutyrate

HRID 355655Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([CH3:13])([CH3:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8].[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]=[C:22]=[O:23].O>C1(C)C=CC=CC=1>[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:21][C:22](=[O:23])[N:5]([C:6]([CH3:12])([CH3:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:4][CH2:3][CH2:2][Cl:1]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of ethyl 2-(3-chloropropylamino)isobutyrate (7.5 g) prepared according to Example 3-(1) in toluene (45 mL) was cooled to 0° C. To the solution was added 2-fluoropheyl isocyanate (5 g), and the mixture was stirred overnight at 0° C. to room temperature. Water was added to the reaction solution and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give 10.9 g of crude ethyl 2-[3-(2-fluorophenyl)-1-(3-chloropropyl)ureido]isobutyrate.

Workup

extractionthe resulting mixture was extracted with ethyl acetate
washThe organic layer was washed with water
dry with materialdried over anhydrous sodium sulfate
distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-d95a1bb2594c449bbcfce8aa7a862794
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05834401

Reaction notes

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