Formaldehyde → HCID 54698217, compound

HRID 2214564Notes

Reaction equation

HRID 2214564 reaction equation
CO[C:3](=[O:20])[C:4]([OH:19])=[CH:5][C:6](=[O:18])[N:7]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[O:8][CH3:9].C=O.CN.ClC1C=C(C=CC=1Cl)[CH2:29][N:30](C)[C:31](C1CN(C)C(=O)C=1O)=O>>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][N:7]([O:8][CH3:9])[C:6]([C:5]2[CH2:29][N:30]([CH3:31])[C:3](=[O:20])[C:4]=2[OH:19])=[O:18])=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 6329MethylamineHCID 54697551N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamideHCID 72395085HCID 72395085, compound2×

Product 1

HCID 54698217HCID 54698217, compoundYield 69%

Procedure

3-[(4-Chlorobenzyl)-methoxy-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 51-B) was treated with paraformaldehyde and methylamine as described in the preparation of Compound 12 to give the title compound as a white solid (69% yield); mp 165° C. dec. 1HNMR 400 MHz (CDCl3) δ (ppm): 3.10 (3H, s, NCH3), 3.72 (3H, s, OCH3), 4.15 (2H, s, NCH2), 4.84 (2H, s, NCH2), 7.25–7.34 (4H, m, aromatics). Anal. calcd for C14H15ClN2O4: C, 54.11; H, 4.87; N, 9.02. Found: C, 53.88; H, 4.71; N, 8.78.

Sources & evidence

ORD record
ord-86aec070ccf1436daca696d2b1a1fa46
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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