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

HRID 2214548Notes

Reaction equation

HRID 2214548 reaction equation
CO[C:3](=[O:21])[C:4]([OH:20])=[CH:5][C:6](=[O:19])[N:7]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=1)[O:8][CH3:9].C=O.CN.ClC1C=C(C=CC=1Cl)[CH2:30][N:31](C)[C:32](C1CN(C)C(=O)C=1O)=O>>[Cl:18][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][C:14]=1[Cl:17])[CH2:10][N:7]([O:8][CH3:9])[C:6]([C:5]1[CH2:30][N:31]([CH3:32])[C:3](=[O:21])[C:4]=1[OH:20])=[O:19]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 6329MethylamineHCID 54697551N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamideHCID 723950783-[(3,4-Dichlorobenzyl)-methoxy-carbamoyl]-2-hydroxy-acrylic acid methyl ester2×

Product 1

HCID 54704645N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N-methoxy-1-methyl-5-oxo-2H-pyrrole-3-carboxamideYield 49%

Procedure

3-[(3,4-Dichlorobenzyl)-methoxy-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 47-C) was treated with paraformaldehyde and methylamine as described in the preparation of Compound 12, yielding the title compound as a white solid (49% yield); mp 149° C. 1HNMR 400 MHz (CDCl3) δ (ppm): 3.11 (3H, s, NCH3), 3.75 (3H, s, OCH3), 4.15 (2H, s, NCH2), 4.82 (2H, s, NCH2), 7.18 (1H, dd, J=2.0 Hz, J=8.2 Hz, aromatic), 7.42 (1H, d, J=8.2 Hz, aromatic), 7.43 (1H, d, J=2.0 Hz, aromatic). Anal. calcd for C14H14Cl2N2O4: C, 48.72; H, 4.09; N, 8.12. Found: C, 48.81; H, 4.04; N, 7.99.

Sources & evidence

ORD record
ord-d7f1170ffd864f0bacfe1341085ebc25
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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