3-Amino-5-methylisoxazole → 4-Hydroxy-2-methyl-N-(5-methyl-3-isoxazolyl)-2H-naphtho [2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide

HRID 1730557Notes

Reaction equation

HRID 1730557 reaction equation
CO[C:3]([C:5]1[N:6]([CH3:22])[S:7](=[O:21])(=[O:20])[C:8]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][C:9]=2[C:10]=1[OH:11])=[O:4].[NH2:23][C:24]1[CH:28]=[C:27]([CH3:29])[O:26][N:25]=1>C1(C)C(C)=CC=CC=1>[OH:11][C:10]1[C:9]2[CH:12]=[CH:13][C:14]3[C:19]([C:8]=2[S:7](=[O:21])(=[O:20])[N:6]([CH3:22])[C:5]=1[C:3]([NH:23][C:24]1[CH:28]=[C:27]([CH3:29])[O:26][N:25]=1)=[O:4])=[CH:18][CH:17]=[CH:16][CH:15]=3

Participants

4

Reactant 2

HCID 661723-Amino-5-methylisoxazoleHCID 546906514-hydroxy-2-methyl-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxylic acid methylester-1,1-dioxide

Product 1

HCID 546959354-Hydroxy-2-methyl-N-(5-methyl-3-isoxazolyl)-2H-naphtho [2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxideYield 57.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

4.8 gm (0.015 mol) of 4-hydroxy-2-methyl-2H-naphtho [2,1-e]-1,2thiazine-3-carboxylic acid methyl ester-1,1-dioxide were reacted with 2.11 gm (0.021 mol) of 3-amino-5-methyl-isoxazole in 250 ml of dry xylene analogous to Example 1, yielding 3.3 gm (57% of theory) of 4-hydroxy-2-methyl-N-(5-methyl-3-isoxazolyl)-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide, m.p. 253° C, after recrystallization from xylene.

Sources & evidence

ORD record
ord-eca9caae48de40b286fe711c7b2c4dd1
Source dataset
uspto-grants-1976_11
Patent number
US03992535

Reaction notes

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