3-Amino-5-methylisoxazole → 5,6-Dihydro-4-hydroxy-2,6-dimethyl-N-(5-methyl-3-isoxazolyl)-1,1-dioxo-2H-1,2,6-thiadiazine-3-carboxamide

HRID 35849

Reaction equation

HRID 35849 reaction equation
[OH:1][C:2]1[CH2:7][N:6]([CH3:8])[S:5](=[O:10])(=[O:9])[N:4]([CH3:11])[C:3]=1[C:12]([O:14]C)=O.[NH2:16][C:17]1[CH:21]=[C:20]([CH3:22])[O:19][N:18]=1>>[OH:1][C:2]1[CH2:7][N:6]([CH3:8])[S:5](=[O:9])(=[O:10])[N:4]([CH3:11])[C:3]=1[C:12]([NH:16][C:17]1[CH:21]=[C:20]([CH3:22])[O:19][N:18]=1)=[O:14]

Participants

3

Reactant 2

HCID 661723-Amino-5-methylisoxazoleHCID 54719676methyl 5,6-dihydro-4-hydroxy-2,6-dimethyl-1,1-dioxo-2H-1,2,6-thiadiazine-3-carboxylate

Product 1

HCID 547196775,6-Dihydro-4-hydroxy-2,6-dimethyl-N-(5-methyl-3-isoxazolyl)-1,1-dioxo-2H-1,2,6-thiadiazine-3-carboxamideYield 49%

Procedure

The synthesis was effected analogously to Example 1 using in each case 1.0 equivalent of methyl 5,6-dihydro-4-hydroxy-2,6-dimethyl-1,1-dioxo-2H-1,2,6-thiadiazine-3-carboxylate and 3-amino-5-methylisoxazole. Recrystallisation from a diisopropyl ether/tetrahydrofuran mixture gives the title compound in a yield of 49%.

Workup

  1. customRecrystallisation from a diisopropyl ether/tetrahydrofuran mixture

Sources & evidence

ORD record
ord-08f064fa14be4ae4821b076e7a759930
Source dataset
uspto-grants-1995_05
Patent number
US05411955

Linked notes

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