Formaldehyde → HCID 54698220, compound

HRID 2214578Notes

Reaction equation

HRID 2214578 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])=[C:13]([F: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>>[F:18][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][C:14]=1[F: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 72395083HCID 72395083, compound

Product 1

HCID 54698220HCID 54698220, compoundYield 53%

Procedure

3-[(3,4-Difluorobenzyl)-methoxy-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 54-D) was treated with paraformaldehyde and methylamine as described in the preparation of Compound 12 to and gave the title compound as a white solid (53% yield); mp 146–147° C. 1HNMR 400 MHz (CDCl3) δ (ppm): 3.11 (3H, s, NCH3), 3.74 (3H, s, OCH3), 4.16 (2H, s, NCH2), 4.79 (2H, s, NCH2), 7.06–7.19 (3H, m, aromatics). Anal. calcd for C14H14F2N2O4: C, 53.84; H, 4.51; N, 8.97. Found: C, 53.82; H, 4.41; N, 8.87.

Sources & evidence

ORD record
ord-9c8556cd054345e68681d07958b8e51e
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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