2,5-Hexanedione → alpha-[2-Chloro-4-(2,3,4,5-tetrahydro-5-methyl-3-oxo-1,2,4-triazin-6-yl)phenoxy]-N-(2,5-dimethyl-1-pyrrolyl)acetamide

HRID 1198911Notes

Reaction equation

[CH2:1]([CH2:5][C:6](=O)[CH3:7])[C:2]([CH3:4])=O.[Cl:9][C:10]1[CH:21]=[C:20]([C:22]2[CH:23]([CH3:29])[NH:24][C:25](=[O:28])[NH:26][N:27]=2)[CH:19]=[CH:18][C:11]=1[O:12][CH2:13][C:14]([NH:16][NH2:17])=[O:15]>C(O)(=O)C>[Cl:9][C:10]1[CH:21]=[C:20]([C:22]2[CH:23]([CH3:29])[NH:24][C:25](=[O:28])[NH:26][N:27]=2)[CH:19]=[CH:18][C:11]=1[O:12][CH2:13][C:14]([NH:16][N:17]1[C:6]([CH3:7])=[CH:5][CH:1]=[C:2]1[CH3:4])=[O:15]

Participants

Conditions

Temperature: 70 °C

Procedure

0.27 g of acetonylacetone was added to a solution of 0.5 g of α-[2-chloro-4-(2,3,4,5-tetrahydro-5-methyl-3-oxo-1,2,4-triazin-6-yl)phenoxy]acetohydrazide (prepared as described in Example 13) dissolved in 5 ml of acetic acid, and the mixture was heated at 70° C. for 4 hours. The acetic acid used as the solvent was removed by evaporation under reduced pressure, and the residue was mixed with water to precipitate crystals. These crystals were collected by filtration, washed with water and dried. The product was purified by column chromatography through silica gel (eluent: a 98:2 by volume mixture of methylene chloride and ethanol), followed by recrystallization from ethanol to give 0.4 g of the title compound melting at 189°-190° C.

Workup

customwas removed by evaporation under reduced pressure
additionthe residue was mixed with water
customto precipitate crystals
filtrationThese crystals were collected by filtration
washwashed with water
customdried
customThe product was purified by column chromatography through silica gel (eluent
additiona 98:2 by volume mixture of methylene chloride and ethanol),
customfollowed by recrystallization from ethanol

Sources & evidence

ORD record: ord-6cce6df8eceb465ab733904b7383fd67
Source dataset: uspto-grants-1990_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04898862

Reaction notes

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