Dimethyl Sulfoxide → 3,6-Dimethyl-4,9-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-10-one

HRID 220764Notes

Reaction equation

HRID 220764 reaction equation
[H-].[Na+:2].C(O[C:6]([C:8]1[CH:9]=[N:10][N:11]([CH3:22])[C:12]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17](C)=[CH:16][C:15]=1[NH2:21])=[O:7])C.[CH3:23][S:24]([CH3:26])=[O:25]>>[CH3:23][S:24]([CH2-:26])=[O:25].[Na+:2].[CH3:22][N:11]1[C:12]2[NH:13][C:14]3[CH:19]=[C:18]([CH3:23])[CH:17]=[CH:16][C:15]=3[NH:21][C:6](=[O:7])[C:8]=2[CH:9]=[N:10]1

Participants

5

Reactant 3

HCID 679Dimethyl Sulfoxide2×HCID 24758Sodium hydrideHCID 575552075-(2-Amino-4-methyl-phenylamino)-1-methyl-1H-pyrazole-4-carboxylic Acid Ethyl Ester

Product 2

HCID 10154010Methane, sulfinylbis-, ion(1-), sodiumHCID 1357360143,6-Dimethyl-4,9-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-10-oneYield 38%

Conditions

Temperature
65 °C

Procedure

Sodium (methylsulphinyl)methanide (22.7 mmol) was prepared from sodium hydride (60% dispersion in oil, 912 mg, 22.7 mmol) and anhydrous dimethyl sulphoxide (5.5 ml) by heating at 65° C. until a solution was observed. To this was added a solution of 5-(2-amino-4-methyl-phenylamino)-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester from Example E2.2 (3.56 g, 13.0 mmol) in anhydrous dimethyl sulphoxide (10 ml), and stirring continued at 65° C. for 30 min. The mixture was then poured into ice (200 ml), the resulting solid collected and purified by flash chromatography on silica gel (eluant; 10% methanol:90% dichloromethane) to yield the title compound (1.12 g, 38%).

Workup

  1. customthe resulting solid collected
  2. custompurified by flash chromatography on silica gel (eluant; 10% methanol:90% dichloromethane)

Sources & evidence

ORD record
ord-1a2ea833a6924951bd3f9c75e6a1db45
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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