Formaldehyde → HCID 54698221, compound

HRID 2214582Notes

Reaction equation

HRID 2214582 reaction equation
CO[C:3](=[O:21])[C:4]([OH:20])=[CH:5][C:6](=[O:19])[N:7]([O:17][CH3:18])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1.C=O.CN.ClC1C=C(C=CC=1Cl)[CH2:30][N:31](C)[C:32](C1CN(C)C(=O)C=1O)=O>>[CH3:18][O:17][N:7]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)[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 72395082HCID 72395082, compound

Product 1

HCID 54698221HCID 54698221, compoundYield 58%

Procedure

2-Hydroxy-3-[methoxy-(4-methoxybenzyl)-carbamoyl]-acrylic acid methyl ester (Compound 55-D) was treated with paraformaldehyde and methylamine as described in the preparation of Compound 12 to give the title compound as a white solid (58% yield); mp 135–137° C. 1HNMR 400 MHz (CDCl3) δ (ppm): 3.09 (3H, s, NCH3), 3.71 (3H, s, OCH3), 3.80 (3H, s, OCH3), 4.14 (2H, s, NCH2), 4.82 (2H, s, NCH2), 6.88 (2H, m, aromatics), 7.27 (2H, m, aromatics). Anal. calcd for C15H18N2O5: C, 58.81; H, 5.92; N, 9.14. Found: C, 58.62; H, 5.88; N, 9.12.

Sources & evidence

ORD record
ord-433efecac3ed4b4d8ace79c8181db6fc
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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