Hydrogen Peroxide → 2-(2-(diethylamino)ethyl)-5-methyl-2H(1)benzothiopyrano[4,3,2-cd]indazole N-oxide monohydrate

HRID 2398973Notes

Reaction equation

HRID 2398973 reaction equation
[CH2:1]([N:3]([CH2:23][CH3:24])[CH2:4][CH2:5][N:6]1[C:14]2[CH:13]=[CH:12][C:11]([CH3:15])=[C:10]3[S:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[C:8]([C:9]=23)=[N:7]1)[CH3:2].[OH:25]O>CC(C)=O>[OH2:25].[CH2:23]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[C:14]2[CH:13]=[CH:12][C:11]([CH3:15])=[C:10]3[S:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[C:8]([C:9]=23)=[N+:7]1[O-:25])[CH3:24]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 322472H-(1)Benzothiopyrano(4,3,2-cd)indazole, 2-(2-(diethylamino)ethyl)-5-methyl-

Product 1

HCID 1317108012-(2-(diethylamino)ethyl)-5-methyl-2H(1)benzothiopyrano[4,3,2-cd]indazole N-oxide monohydrate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-(2-(diethylamino)ethyl)-5-methyl-2H(1)benzothiopyrano[4,3,2-cd]indazole (0.17 g.) in acetone (4 ml.) was added 0.2 ml. of 30% aqueous hydrogen peroxide. The solution was left at room temperature overnight and then evaporated to dryness under reduced pressure. The residue was crystallized from acetone-ether to give 2-(2-(diethylamino)ethyl)-5-methyl-2H(1)benzothiopyrano[4,3,2-cd]indazole N-oxide monohydrate, m.p. 123°-124° (decomp.). This compound, when crystallized in the presence of hydrochloric acid, gave a water-soluble monohydrochloride salt which darkened and decomposed at temperatures above 150°.

Workup

  1. customevaporated to dryness under reduced pressure
  2. customThe residue was crystallized from acetone-ether

Sources & evidence

ORD record
ord-e878ea2ffa5c4f789908c5385d1cd4fb
Source dataset
uspto-grants-1977_05
Patent number
US04026899

Reaction notes

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