Dimethyl Sulfoxide → 4-Nitro-6-(trifluoromethyl)-2H-1,3-benzodithiol-2-one

HRID 46800

반응식

HRID 46800 반응식
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([N+]([O-])=O)[C:5]=1Cl)([O-:3])=[O:2].CS(C)=[O:20].CN(C)[C:24](=[S:26])[SH:25].[Na].O>C(Cl)(Cl)Cl>[N+:1]([C:4]1[C:5]2[S:26][C:24](=[O:20])[S:25][C:6]=2[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-:3])=[O:2]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 98094-Chloro-3,5-dinitrobenzotrifluorideHCID 24189202Sodium dimethyldithiocarbamic acid

생성물 1

HCID 123611104-Nitro-6-(trifluoromethyl)-2H-1,3-benzodithiol-2-one수율 43.3%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

The compound of Example I is prepared in the following manner: To a magnetically stirred solution of 16.2 g (60 mmoles) 2,6-dinitro-4-trifluoromethylchlorobenzene in 60 ml. dimethylsulfoxide was added dropwise a solution of 10.74 g (60 mmoles) sodium dimethyldithiocarbamic acid. The reaction is mildly exothermic and accompanied by evolution of oxides of nitrogen. After allowing the reaction mixture to stir for 3 hours, 450 ml. water and 225 ml. chloroform are added and, after shaking well in an extraction funnel, the chloroform extract was withdrawn and the aqueous phase similarly extracted with two more 220 ml. portions of chloroform. The combined chloroform extract was washed thrice with 750 ml. portions of water, and dried over anhy. Na2SO4. After removing the solvent on a rotary evaporator, the residue was chromatographed over 180 g Silica-Gel. Elution with hexane-benzene (1:1) yielded 7.3 g (43.3%) 4-nitro-6-trifluoromethyl-1,3-benzodithiole-2-one, m.p. 103°-107° C. One recrystallization from ethanol yielded product, m.p. 111°-112° C.

후처리

  1. customThe compound of Example I is prepared in the following manner
  2. stirringafter shaking well in an extraction funnel
  3. extractionthe chloroform extract
  4. customwas withdrawn
  5. extractionthe aqueous phase similarly extracted with two more 220 ml
  6. extractionThe combined chloroform extract
  7. washwas washed thrice with 750 ml
  8. dry with materialportions of water, and dried over anhy
  9. customAfter removing the solvent
  10. customon a rotary evaporator
  11. customthe residue was chromatographed over 180 g Silica-Gel
  12. washElution with hexane-benzene (1:1)

출처 및 근거

ORD 기록
ord-136e956ca48f4a4d83b681b4519b042c
출처 데이터셋
uspto-grants-1979_11
특허 번호
US04175186

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