Formaldehyde → HCID 54698230, compound

HRID 2214621Notes

Reaction equation

HRID 2214621 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]([CH3:17])=[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[CH3:17])[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 72395065HCID 72395065, compound2×

Product 1

HCID 54698230HCID 54698230, compoundYield 54%

Procedure

3-[(3-Fluoro-4-methylbenzyl)-methoxy-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 65-A) was treated with paraformaldehyde and methylamine as described in the preparation of Compound 12 to give the title compound as white crystals (54% yield); mp 145° C. 1HNMR 400 MHz (CDCl3) δ (ppm): 2.26 (3H, broad s, CH3), 3.11 (3H, s, NCH3), 3.73 (3H, s, OCH3), 4.16 (2H, s, NCH2), 4.83 (2H, s, NCH2), 6.99 (2H, m, aromatics), 7.16 (1H, m, aromatic). Anal. calcd for C15H17FN2O4: C, 58.44; H, 5.56; N, 9.09. Found: C, 58.16; H, 5.44; N, 8.88.

Sources & evidence

ORD record
ord-d8efa61e6c18453c8b45a66e578ea103
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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