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2,8-Dibromo-3,7-dinitrodibenzothiophene-5-oxide → Dibenzothiophene, 2,8-dibromo-3,7-dinitro-, 5,5-dioxide

HRID 376731
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HRID 376731 반응식
[Br:1][C:2]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:5]2[S:6](=[O:17])[C:7]3[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([Br:16])=[CH:9][C:8]=3[C:4]=2[CH:3]=1.BrC1C([N+]([O-])=O)=CC2S(=[O:36])C3C=CC(Br)=CC=3C=2C=1.I([O-])(=O)(=O)=O.[Na+]>[Ru](Cl)(Cl)Cl.O.O1CCCC1.C(#N)C.O1CCOCC1.C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:5]2[S:6](=[O:36])(=[O:17])[C:7]3[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([Br:16])=[CH:9][C:8]=3[C:4]=2[CH:3]=1
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참가 물질

10

반응물 3

HCID 158859092,8-Dibromo-3,7-dinitrodibenzothiophene-5-oxideHCID 158859102,8-Dibromo-3-nitrodibenzothiophene-5-oxideHCID 23667635Sodium periodate

생성물 1

HCID 4571975Dibenzothiophene, 2,8-dibromo-3,7-dinitro-, 5,5-dioxide

시약·촉매·용매 6

HCID 61850Ruthenium trichloride촉매
HCID 962
Water
용매
3회
HCID 5943Carbon Tetrachloride용매
HCID 6342Acetonitrile용매2회
HCID 8028Tetrahydrofuran용매
HCID 312751,4-Dioxane용매

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온도
45 °C

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.

후처리

  1. additionwas treated in a heterogeneous solvent mixture which

출처 및 근거

ORD 기록
ord-15bd87a547b04673893d78ec055368d6
출처 데이터셋
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06022307

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