Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2214514Generated: October 31, 2026

Formaldehyde → N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N-methyl-1-[2-(methylamino)ethyl]-5-oxo-2H-pyrrole-3-carboxamide

https://huagongshe.com/reaction/2214514

Reaction equation

Participants

RoleNameHCIDCharge
ReactantFormaldehydeHCID 712—
ReactantPropylenediamineHCID 6567—
ReactantN-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamideHCID 54697551—
ReactantHCID 69655739HCID 69655739—
ProductN-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N-methyl-1-[2-(methylamino)ethyl]-5-oxo-2H-pyrrole-3-carboxamideHCID 546981944%

Reaction Steps

3-[(3,4-Dichloro-benzyl-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 12-B) was treated with paraformaldehyde and methyl-ethane-1,2-diamine as described in the preparation of Compound 12. The title compound was triturated with EtOAc to give a white solid (7.8 mg, 4% yield). 1H NMR (300 MHz, CDCl3) δ: 9.14, (bs, 1H), 7.40, (d, 1H, J=8.05), 7.34 (s, 1H), 7.11 (dd, 1H, J=8.05, J=1.10), 4.58, (s, 2H), 4.34, (s, 2H), 3.94 (m, 2H), 3.25 (m, 2H), 3.03 (s, 3H), 2.78 (s, 3H). HRMS (M+H) calcd for C16H19N3Cl2O3: 372.0881. found: 372.0886.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07109186B2
Source datasetuspto-grants-2006_09
ORD IDord-82f0cb2e977a4a569371f52df5ea9c0d
Source noteuspto-grants-2006_09