1,3,4-Thiadiazol-2-amine → 4-Hydroxy-2-methyl-N-(1,3,4-thiadiazolyl)-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide

HRID 1730556Notes

Reaction equation

HRID 1730556 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]=[N:27][N:28]=1>C(Cl)CCl.C(OCC)(=O)C>[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]=[N:27][N:28]=1)=[O:2])=[CH:18][CH:17]=[CH:16][CH:15]=3

Participants

4

Reactant 2

HCID 199091,3,4-Thiadiazol-2-amineHCID 546906514-hydroxy-2-methyl-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxylic acid methylester-1,1-dioxide

Product 1

HCID 546959314-Hydroxy-2-methyl-N-(1,3,4-thiadiazolyl)-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxideYield 41%

Reagents, catalysts & solvents 1

HCID 20136152Ethylene chloride ethyl acetateSolvent

Procedure

4-Hydroxy-2-methyl-N-(1,3,4-thiadiazolyl)-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide was prepared analogous to Example 1 from 4-hydroxy-2-methyl-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxylic acid methylester-1,1-dioxide and 2-amino-1,3,4-thiadiazole. Yield: 41% of theory; m.p.217°-219° C (decomp.; from ethylene chloride/ethyl acetate).

Sources & evidence

ORD record
ord-0e535e7f45c44230a8a3aea87576e2e3
Source dataset
uspto-grants-1976_11
Patent number
US03992535

Reaction notes

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