Formaldehyde → N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamide

HRID 2214511Notes

Reaction equation

[CH3:1][NH2:2].O1CCCC1.[CH2:8]=O.CO[C:12](=[O:29])[C:13]([OH:28])=[CH:14][C:15](=[O:27])[N:16]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=1)[CH3:17]>C(O)C>[Cl:26][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][C:22]=1[Cl:25])[CH2:18][N:16]([CH3:17])[C:15]([C:14]1[CH2:1][N:2]([CH3:8])[C:12](=[O:29])[C:13]=1[OH:28])=[O:27]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 2 M methylamine in tetrahydrofuran (0.5 ml, 1.0 mmol) was added to a mixture of paraformaldehyde (0.3 g, 1.0 mmol, equivalent of formaldehyde) in anhydrous ethanol (1 ml) and the resulting mixture was heated at 60° C. for 5 min. Then a solution of 3-[(3,4-dichlorobenzyl)-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester (0.318 g, 1.0 mmol) in ethanol (3 ml) was added all at once and the resulting mixture was maintained at 60° C. for another 20 min. The reaction mixture was then quenched by the addition of ethyl acetate and pH 2 phosphate buffer. The organic phase was washed with brine, dried (anhydrous magnesium sulfate) and concentrated under reduced pressure. Recrystallization of the solid residue from a mixture of ethyl acetate and hexane gave 0.180 g (54% yield) of the title material as a white solid: mp 148–150° C.

Workup

temperaturewas maintained at 60° C. for another 20 min
customThe reaction mixture was then quenched by the addition of ethyl acetate and pH 2 phosphate buffer
washThe organic phase was washed with brine
dry with materialdried (anhydrous magnesium sulfate)
concentrationconcentrated under reduced pressure
customRecrystallization of the solid residue
additionfrom a mixture of ethyl acetate and hexane

Sources & evidence

ORD record: ord-704a4a667568418b99540225f86f3ee8
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109186B2

Reaction notes

Loading…