Formaldehyde → HCID 54698226, compound

HRID 2214602Notes

Reaction equation

HRID 2214602 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]([F:17])=[CH:13][C:12]=1[F:18])[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>>[F:18][C:12]1[CH:13]=[C:14]([F:17])[CH:15]=[CH:16][C:11]=1[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 72395069HCID 72395069, compound

Product 1

HCID 54698226HCID 54698226, compoundYield 55%

Procedure

3-[(2,4-Difluorobenzyl)-methoxy-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 60-D) was treated with paraformaldehyde and methylamine as described in the preparation of Compound 12 to give the title compound as a white solid (55% yield); mp 141–149° C., dec. 1HNMR 400 MHz (CDCl3) δ (ppm): 3.1 (3H, s, NCH3), 3.77 (3H, s, OCH3), 4.14 (2H, s, NCH2), 4.92 (2H, s, NCH2), 6.8–6.9 (2H, m, aromatics), 7.35–7.41 (1H, m, aromatic).

Sources & evidence

ORD record
ord-a3c27a6838d4488092376580fda7a29e
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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