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Methanol → 2,8-dibromo-5,5-dioxo-5H-5lambda6-dibenzothiophene-3,7-diamine

HRID 376732
Notes
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Reaction equation

HRID 376732 reaction equation
[Br:1][C:2]1[C:20]([N+:21]([O-])=O)=[CH:19][C:5]2[S:6](=[O:18])(=[O:17])[C:7]3[CH:12]=[C:11]([N+:13]([O-])=O)[C:10]([Br:16])=[CH:9][C:8]=3[C:4]=2[CH:3]=1.[Sn](Cl)Cl.[H][H].CO>[Pd].[Fe].[Zn].C(O)(=O)C.COCCO.C(O)CC.C(O)C>[Br:1][C:2]1[C:20]([NH2:21])=[CH:19][C:5]2[S:6](=[O:18])(=[O:17])[C:7]3[CH:12]=[C:11]([NH2:13])[C:10]([Br:16])=[CH:9][C:8]=3[C:4]=2[CH:3]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

12

Reactant 4

HCID 887MethanolHCID 24479Stannous ChlorideHCID 4571975Dibenzothiophene, 2,8-dibromo-3,7-dinitro-, 5,5-dioxideHCID 178418361HCID 178418361, compound

Product 1

HCID 158859562,8-dibromo-5,5-dioxo-5H-5lambda6-dibenzothiophene-3,7-diamine

Reagents, catalysts & solvents 7

HCID 23925
Iron
Catalyst
HCID 23938PalladiumCatalyst
HCID 23994ZincCatalyst
HCID 176Acetic AcidSolvent
HCID 702EthanolSolvent
HCID 10311-PropanolSolvent
HCID 80192-MethoxyethanolSolvent

Procedure

Referring to Scheme II, a mixture of 2,8-dibromo-3,7-dinitrodibenzothiophene-5-oxide 3a and 2,8-dibromo-3-nitrodibenzothiophene-5-oxide 3b was treated in a heterogeneous solvent mixture which include but not limited to acetonitrile, carbon tetrachloride and water, p-dioxane and water, acetonitrile, tetrahydrofuran and water; with an oxidizing agent which include but not limited to sodium periodate and ruthenium(III) chloride; stirred at a temperature range from 15-75° C. until completion as indicated by TLC to yield 2,8-dibromo-3,7-dinitrodibenzothiophene-5,5-dioxide 9 as the isolated product. Treating 2,8-dibromo-3,7-dinitrodibenzothiophen-5,5-dioxide 9 with a reducing agent which include but are not limited to powdered iron, tin (II) chloride, zinc metal or palladium on charcoal with hydrogen in alcoholic solvents which include but are not limited to methyl alcohol, ethyl alcohol, propyl alcohol or 2-methoxy-ethanol and the like; and an organic acid which includes but is not limited to acetic acid; at a temperature range from 50-120° C. for about 2 hours or until completion to give 2,8-dibromo-5,5-dioxo-5H-5λ6 -dibenzothiophene-3,7-diamine 10.

Sources & evidence

ORD record
ord-7a672bb9033e49159e7c343b3b16934d
Source dataset
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06022307

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes