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Sodium Azide → 3-bromo-5-nitrophenyl-1-methyl-1H-tetrazole

HRID 1422392
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HRID 1422392 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[C:5]([NH:7][CH3:8])=O.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.[N-:30]=[N+:31]=[N-:32].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[N:7]([CH3:8])[N:32]=[N:31][N:30]=2)[CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1
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참가 물질

6

반응물 4

HCID 33557Sodium AzideHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 222526863-Bromo-N-methyl-5-nitrobenzamide

생성물 1

HCID 222526903-bromo-5-nitrophenyl-1-methyl-1H-tetrazole수율 44.1%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

To a solution of 3-bromo-N-methyl-5-nitro-benzamide (0.6 g) in DCM (15 ml) at −15° C. was added triflic anhydride (0.6 ml) and the reaction stirred for 30 min. Sodium azide (226 mg) was added and the reaction allowed to warm to room temperature and stirred further overnight. NaHCO3(aq) was added to neutralise the reaction and the mixture extracted into EtOAc. The organic layer was separated, dried and concentrated in vacuum and the residue purified by flash chromatography (9:1 to 2:8 cyclohexane:EtOAc) to give the title compound (290 mg). Rf=0.51 (3:2 cyclohexane:EtOAc).

후처리

  1. stirringstirred further overnight
  2. customthe reaction
  3. extractionthe mixture extracted into EtOAc
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated in vacuum
  7. customthe residue purified by flash chromatography (9:1 to 2:8 cyclohexane:EtOAc)

출처 및 근거

ORD 기록
ord-4d35fc24975a46cd8faf905fd7ed430b
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
USRE045323E1

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