Formaldehyde → HCID 54698235, compound

HRID 2214629Notes

Reaction equation

HRID 2214629 reaction equation
CC1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([CH:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH3:14])[O:11][CH3:12])=[O:9])[C:4](=[O:22])O1.C=O.CN.ClC1C=C(C=CC=1Cl)[CH2:32][N:33](C)[C:34](C1CN(C)C(=O)C=1O)=O>CO>[F:21][C:18]1[CH:17]=[CH:16][C:15]([CH:13]([N:10]([O:11][CH3:12])[C:8]([C:7]2[CH2:32][N:33]([CH3:34])[C:4](=[O:22])[C:5]=2[OH:6])=[O:9])[CH3:14])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6329MethylamineHCID 54697551N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamideHCID 73855562HCID 73855562, compound

Product 1

HCID 54698235HCID 54698235, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(2,2-Dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-N-[1-(4-fluorophenyl)-ethyl]-N-methoxy-acetamide, prepared using the methods described in the previous examples, was treated in methanol with paraformaldehyde and methylamine as described in the preparation Compound 12 to give the title compound as a white solid (47% yield); mp 136–138° C. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.68 (3H, d, J=7.1 Hz, CH3), 3.1 (3H, s, NCH3), 3.49 (3H, s, OCH3), 4.13 (2H, AB system, JAB=18.2 Hz, Δv=45.7 Hz, NCH2), 5.75 (1H, q, J=7.1 Hz, CH), 7.06 (2H, m, aromatics), 7.42 (2H, m, aromatics). Anal. calcd for C15H17FN2O4: C, 58.43; H, 5.55; N, 9.08. Found: C, 58.40; H, 5.38; N, 9.01.

Sources & evidence

ORD record
ord-25f98e870c0a41c2847ebcdc81443a45
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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