Formaldehyde → 4-Hydroxy-1-(4-hydroxy-butyl)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid (3,4-dichloro-benzyl)-methoxy-amide

HRID 2214680Notes

Reaction equation

HRID 2214680 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]([Cl:17])=[C:13]([Cl:18])[CH:12]=1)[O:8][CH3:9].[CH2:22]=O.[NH2:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29]>>[Cl:18][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][C:14]=1[Cl:17])[CH2:10][N:7]([O:8][CH3:9])[C:6]([C:5]1[CH2:22][N:24]([CH2:25][CH2:26][CH2:27][CH2:28][OH:29])[C:3](=[O:21])[C:4]=1[OH:20])=[O:19]

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 258684-Amino-1-butanolHCID 723950783-[(3,4-Dichlorobenzyl)-methoxy-carbamoyl]-2-hydroxy-acrylic acid methyl ester

Product 1

HCID 547046404-Hydroxy-1-(4-hydroxy-butyl)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid (3,4-dichloro-benzyl)-methoxy-amideYield 36%

Procedure

3-[(3,4-Dichloro-benzyl)-methoxy-carbamoyl]-2-hydroxy-acrylic acid methyl ester, paraformaldehyde and 4-amino-butanol were reacted according to the method described for compounds 792–808 to give the tile compound as a yellow oil (0.015 g, 36% yield). 1HNMR (300 MHz, CDCl3) δ: 7.43–7.40 (2H, m), 7.18 (1H, dd, J=8.42,1.83 Hz), 4.81 (2H, s), 4.14 (2H, s), 3.74 (3H, s), 3.63 (2H, t, J=6.40 Hz), 3.51 (2H, t, J=4.01 Hz), 1.68–1.53 (4H, M), 1.43–1.33 (2H, m).

Sources & evidence

ORD record
ord-2e9de87594b44864bdc6b732a46c3c64
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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