Formaldehyde → HCID 54698233, compound

HRID 2214627Notes

Reaction equation

HRID 2214627 reaction equation
[C:1]([O:5][C:6](=[O:28])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]([C:17](=[O:27])[CH:18]=[C:19]2[C:23](=O)[O:22]C(C)(C)[O:20]2)[O:15][CH3:16])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C=O.CN.ClC1C=C(C=CC=1Cl)[CH2:37][N:38](C)[C:39](C1CN(C)C(=O)C=1O)=O>CO>[C:1]([O:5][C:6](=[O:28])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]([C:17]([C:18]2[CH2:37][N:38]([CH3:39])[C:23](=[O:22])[C:19]=2[OH:20])=[O:27])[O:15][CH3:16])=[CH:9][CH:8]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6329MethylamineHCID 54697551N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamideHCID 74058496HCID 74058496, compound

Product 1

HCID 54698233HCID 54698233, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-({[2-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-acetyl]-methoxyamino}-methyl)-benzoic acid tert-butyl ester, prepared using the methods described in the previous examples, was treated in methanol with paraformaldehyde and methylamine as described in the preparation of Compound 12 to give the title compound as a white solid (40% yield); mp 157–160° C. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.58 (9H, s, t-Bu), 3.11 (3H, s, NCH3), 3.72 (3H, s, OCH3), 4.16 (2H, s, NCH2), 4.92 (2H, s, NCH2), 7.37 (2H, d, J=8 Hz, aromatics), 7.97 (2H, d, J=8 Hz, aromatics), 11.55 (1H, broad s, OH).

Sources & evidence

ORD record
ord-be12bf793c9646b499a0ee85ec6e7428
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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