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Dimethylcarbamoyl Chloride → 3,5-Dibromopicolinonitrile

HRID 917619
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HRID 917619 반응식
[Br:1][C:2]1[CH:3]=[N+:4]([O-])[CH:5]=[C:6]([Br:8])[CH:7]=1.C[Si]([C:14]#[N:15])(C)C.CN(C)C(Cl)=O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[C:14]([C:3]1[C:2]([Br:1])=[CH:7][C:6]([Br:8])=[CH:5][N:4]=1)#[N:15]
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참가 물질

6

반응물 4

HCID 6598Dimethylcarbamoyl Chloride2회HCID 82115Trimethylsilyl cyanide2회HCID 516892Sodium BicarbonateHCID 6200033,5-Dibromopyridine N-oxide

생성물 1

HCID 123612023,5-Dibromopicolinonitrile

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 3,5-dibromopyridine N-oxide (prepared in the above (1)) 2.26 g, trimethylsilylcyanide 1.06 g and dimethylcarbamic acid chloride 1.15 g in methylene chloride 25 ml is refluxed under heating for 1 day. To the mixture are added trimethylsilylcyanide 443 mg and dimethylcarbamic acid chloride 480 mg, and the mixture is refluxed under heating for 20 hours. An aqueous sodium hydrogen carbonate solution is added to the reaction mixture cooled, and the mixture is extracted with methylene chloride. The combined extract is washed, dried and the solvent is removed in vacuo. The residue is purified by silica gel chromatography (solvent; n-hexane:ethyl acetate=1:1) to give 2-cyano-3,5-dibromopyridine 1.38 g. mp 109-112° C.

후처리

  1. temperatureis refluxed
  2. temperatureunder heating for 1 day
  3. temperaturethe mixture is refluxed
  4. temperatureunder heating for 20 hours
  5. temperaturecooled
  6. extractionthe mixture is extracted with methylene chloride
  7. extractionThe combined extract
  8. washis washed
  9. customdried
  10. customthe solvent is removed in vacuo
  11. customThe residue is purified by silica gel chromatography (solvent; n-hexane:ethyl acetate=1:1)

출처 및 근거

ORD 기록
ord-d65113fd895c4bb9b73064aaf4f95776
출처 데이터셋
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07273868B2

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