Formaldehyde → HCID 54698215, compound

HRID 2214556Notes

Reaction equation

HRID 2214556 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][CH:14]=[C:13]([F:17])[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>>[F:17][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[CH2:10][N:7]([O:8][CH3:9])[C:6]([C:5]1[CH2:29][N:30]([CH3:31])[C:3](=[O:20])[C:4]=1[OH:19])=[O:18]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 6329MethylamineHCID 54697551N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamideHCID 72395067HCID 72395067, compound2×

Product 1

HCID 54698215HCID 54698215, compoundYield 60%

Procedure

3-[(3-Fluorobenzyl)-methoxy-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 49-C) was reacted with paraformaldehyde and methylamine as described in the preparation of Compound 12 to give the title compound as a white solid (60% yield); mp 119° C. dec. 1HNMR 400 MHz (CDCl3) δ (ppm): 3.11 (3H, s, NCH3), 3.74 (3H, s, OCH3), 4.17 (2H, s, NCH2), 4.87 (2H, s, NCH2), 6.99–7.35 (4H, m, aromatics). Anal. calcd for C14H15FN2O4: C, 57.14; H, 5.14; N, 9.52. Found: C, 57.04; H, 5.02; N, 9.42.

Sources & evidence

ORD record
ord-8c1a901c539d44f783253df2e63fc92c
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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