1,2-Dichloroethane → 4-hydroxy-2-methyl-N-(2-thiazolyl)-2H-naphtho [2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide

HRID 1730547Notes

Reaction equation

HRID 1730547 reaction equation
C[O:2][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.[NH2:23][C:24]1[S:25][CH:26]=[CH:27][N:28]=1.C(Cl)CCl>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[S:25][CH:26]=[CH:27][N:28]=1)=[O:2])=[CH:18][CH:17]=[CH:16][CH:15]=3

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 21552-AminothiazoleHCID 546906514-hydroxy-2-methyl-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxylic acid methylester-1,1-dioxide

Product 1

HCID 547184104-hydroxy-2-methyl-N-(2-thiazolyl)-2H-naphtho [2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxideYield 56.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

19.8 gm (0.062 mol) of 4-hydroxy-2-methyl-2H-naphtho [2,1-e]-1,2-thiazine-3-carboxylic acid methyl ester-1,1-dioxide were reacted with 9.3 gm (0.093 mol) of 2-amino-thiazole in 500 ml of xylene analogous to Example 1 and yielded 13.5 gm (56% of theory) of 4-hydroxy-2-methyl-N-(2thiazolyl)-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide, m.p. 248°-249° C (decomp.; from ethylene chloride).

Sources & evidence

ORD record
ord-9a9d8bef1ab3488285286a87597d6f71
Source dataset
uspto-grants-1976_11
Patent number
US03992535

Reaction notes

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