2-Amino-4,6-dimethylpyridine → HCID 12821987, compound

HRID 847657Notes

Reaction equation

HRID 847657 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[N:10]([S:13]([C:16]1[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19])(=[O:15])=[O:14])=[C:11]=[O:12]>C(Cl)Cl>[CH3:8][C:6]1[CH:5]=[C:4]([CH3:9])[N:3]=[C:2]([NH:1][C:11]([NH:10][S:13]([C:16]2[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=2[C:18]([O:20][CH3:21])=[O:19])(=[O:15])=[O:14])=[O:12])[CH:7]=1

Participants

4

Reactant 2

HCID 215072-Amino-4,6-dimethylpyridineHCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl ester

Product 1

HCID 12821987HCID 12821987, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1.2 g of 2-amino-4,6-dimethylpyridine in 30 ml of methylene chloride at ambient temperature was added dropwise, with stirring 2.4 g of methyl 2-isocyanatosulfonylbenzoate. After stirring for one hour at room temperature a solid precipitated from the mixture. Filtration yielded 1.8 g of a crystalline white solid which melted at 181°-182° C. and showed absorption peaks by infrared spectroscopy at 1750, 1700, 1630 and 1580 cm-1. The nuclear magnetic resonance spectrum (60 mc) showed peaks at 7-8.6 δ (multiplet) for o-substituted benzene, 4.36 δ (singlet) for OCH3 and 2.76, 2.7 δ (singlets) for the two methyl groups on the pyridine ring.

Workup

  1. customprecipitated from the mixture
  2. filtrationFiltration

Sources & evidence

ORD record
ord-c873921bdc85495199b315318064d0c8
Source dataset
uspto-grants-1981_10
Patent number
US04293330

Reaction notes

Loading…