Formaldehyde → HCID 54698222, compound

HRID 2214587Notes

Reaction equation

HRID 2214587 reaction equation
CO[C:3](=[O:20])[C:4]([OH:19])=[CH:5][C:6](=[O:18])[N:7]([O:16][CH3:17])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15].C=O.CN.ClC1C=C(C=CC=1Cl)[CH2:29][N:30](C)[C:31](C1CN(C)C(=O)C=1O)=O>>[CH3:17][O:16][N:7]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15])[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 72395072HCID 72395072, compound

Product 1

HCID 54698222HCID 54698222, compoundYield 61%

Procedure

2-Hydroxy-3-[methoxy-(2-methylbenzyl)-carbamoyl]-acrylic acid methyl ester (Compound 56-D) was treated with paraformaldehyde and methylamine as described in the preparation of Compound 12 to give the title compound as a white solid (61% yield); mp 153–154° C. 1HNMR 400 MHz (CDCl3) δ (ppm): 2.39 (3H, s, CH3), 3.13 (3H, s, NCH3), 3.67 (3H, s, OCH3), 4.19 (2H, s, NCH2), 4.95 (2H, s, NCH2), 7.2–7.3 (4H, m, aromatics), 11.7 (1H, broad s, OH). Anal. calcd for C15H18N2O4: C, 62.05; H, 6.24; N, 9.65. Found: C, 61.79; H, 6.30; N, 9.58.

Sources & evidence

ORD record
ord-382b9e0be36c44fb93244a423a684180
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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