4-Fluoroaniline → 2,5-Dihydro-2,5-dimethyl-N-(4-fluoro-phenyl)-4-hydroxy-1,2-thiazino[5,6-b]indole-3-carboxamide-1,1-dioxide

HRID 2164110Notes

Reaction equation

HRID 2164110 reaction equation
[CH3:1][N:2]1[C:15]([C:16](OCCCC)=[O:17])=[C:14]([OH:23])[C:5]2[N:6]([CH3:13])[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:4]=2[S:3]1(=[O:25])=[O:24].[F:26][C:27]1[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=1>C1(C)C(C)=CC=CC=1>[CH3:1][N:2]1[C:15]([C:16]([NH:31][C:30]2[CH:32]=[CH:33][C:27]([F:26])=[CH:28][CH:29]=2)=[O:17])=[C:14]([OH:23])[C:5]2[N:6]([CH3:13])[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:4]=2[S:3]1(=[O:25])=[O:24]

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 54684961n-Butyl 2,5-dihydro-2,5-dimethyl-4-hydroxy-1,2-thiazino[5,6-b]indole-3-carboxylate-1,1-dioxide

Product 1

HCID 546849852,5-Dihydro-2,5-dimethyl-N-(4-fluoro-phenyl)-4-hydroxy-1,2-thiazino[5,6-b]indole-3-carboxamide-1,1-dioxideYield 68%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2,5-Dihydro-2,5-dimethyl-N-(4-fluoro-phenyl)-4-hydroxy-1,2-thiazino[5,6-b]indole-3-carboxamide-1,1-dioxide was prepared analogous to Example 9 from n-butyl 2,5-dihydro-2,5-dimethyl-4-hydroxy-1,2-thiazino[5,6-b]indole-3-carboxylate-1,1-dioxide and 4-fluoro-aniline in xylene; M.p.: 271°-272° C. (decomp.); Yield: 68% of theory;

Sources & evidence

ORD record
ord-abbb54c8efb74c8b8ccda593ad4447b1
Source dataset
uspto-grants-1979_01
Patent number
US04137313

Reaction notes

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