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

HRID 1730566Notes

Reaction equation

HRID 1730566 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH3:23])[S:8](=[O:22])(=[O:21])[C:9]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][C:10]=2[C:11]=1[OH:12])=O)C.[Cl:24][C:25]1[CH:26]=[C:27]([CH:29]=[CH:30][CH:31]=1)[NH2:28]>C(Cl)CCl>[Cl:24][C:25]1[CH:26]=[C:27]([NH:28][C:4]([C:6]2[N:7]([CH3:23])[S:8](=[O:21])(=[O:22])[C:9]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]=[CH:13][C:10]=3[C:11]=2[OH:12])=[O:3])[CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 79323-ChloroanilineHCID 681419124-hydroxy-2-methyl-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxylic acid ethyl ester-1,1-dioxide

Product 1

HCID 54695958N-(3-Chloro-phenyl)-4-hydroxy-2-methyl-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxideYield 71%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

N-(3-Chloro-phenyl)-4-hydroxy-2-methyl-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 ethyl ester-1,1-dioxide and 3-chloroaniline. Yield: 71% of theory; m.p. 248°-249° C (decomp.; from ethylene chloride).

Sources & evidence

ORD record
ord-107e738f52ec414d9454edc0be764687
Source dataset
uspto-grants-1976_11
Patent number
US03992535

Reaction notes

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