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

HRID 1730578Notes

Reaction equation

HRID 1730578 reaction equation
[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][C:10]3[C:15]([C:6]=2[S:5](=[O:17])(=[O:16])[NH:4][C:3]=1[C:18]([NH2:20])=[O:19])=[CH:14][CH:13]=[CH:12][CH:11]=3.[CH:21]([Cl:24])(Cl)Cl.[H][H]>[Pd].CO>[Cl:24][C:21]1[CH:18]=[C:3]([NH:20][C:18]([C:3]2[NH:4][S:5](=[O:17])(=[O:16])[C:6]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH:9]=[CH:8][C:7]=3[C:2]=2[OH:1])=[O:19])[CH:2]=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 6212ChloroformHCID 681429134-hydroxy-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxideHCID 178418361HCID 178418361, compound

Product 1

HCID 54695941N-(3-chloro-phenyl)-4-hydroxy-2H-naphtho[2,1-e]1,2-thiazine-3-carboxamide-1,1-dioxideYield 57%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 490 mgm (1 millimol) of 2-benzyl-N-3-chloro-phenyl)-4-hydroxy-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide in 100 ml of a mixture of chloroform and methanol (2:1) was hydrogenated in the presence of 500 mgm of a palladium-on-charcoal catalyst (10%) at a hydrogen pressure of 3 atmospheres for 10 hours. The reaction mixture was then filtered, and the catalyst left on the filter was copiously washed with hot chloroform. The combined filtrates were evaporated, and the residue was purified by columnchromatography (silicagel particle size 0.2-0.5 mm), using chloroform/methanol (20:1) as the eluant. 230 mgm (57% of theory) of N-(3-chloro-phenyl)-4-hydroxy-2H-naphtho[2,1-e]1,2-thiazine-3-carboxamide-1,1-dioxide, m.p. 262° C (decomp.), were obtained.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. waitthe catalyst left on the filter
  3. washwas copiously washed with hot chloroform
  4. customThe combined filtrates were evaporated
  5. customthe residue was purified by columnchromatography (silicagel particle size 0.2-0.5 mm)

Sources & evidence

ORD record
ord-a644cc8250bf4c7cb2cccf8c5d6c32d8
Source dataset
uspto-grants-1976_11
Patent number
US03992535

Reaction notes

Loading…