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

HRID 376732
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HRID 376732 반응식
[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
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참가 물질

12

반응물 4

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

생성물 1

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

시약·촉매·용매 7

HCID 23925Iron
촉매
HCID 23938Palladium촉매
HCID 23994Zinc촉매
HCID 176Acetic Acid용매
HCID 702Ethanol용매
HCID 10311-Propanol용매
HCID 80192-Methoxyethanol용매

실험 절차

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.

출처 및 근거

ORD 기록
ord-7a672bb9033e49159e7c343b3b16934d
출처 데이터셋
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06022307

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