Sodium Azide → 5-Chloro-4-nitrothiophene-2-carbonyl azide

HRID 1192276노트

반응식

HRID 1192276 반응식
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[S:12][C:11]([C:13](O)=[O:14])=[CH:10][C:9]=1[N+:16]([O-:18])=[O:17].[N-:19]=[N+:20]=[N-:21].[Na+]>ClCCl.C(OCC)(=O)C>[Cl:7][C:8]1[S:12][C:11]([C:13]([N:19]=[N+:20]=[N-:21])=[O:14])=[CH:10][C:9]=1[N+:16]([O-:18])=[O:17]

참가 물질

6

반응물 3

HCID 33557Sodium AzideHCID 65578Oxalyl chlorideHCID 132055635-Chloro-4-nitrothiophene-2-carboxylic acid

생성물 1

HCID 602075075-Chloro-4-nitrothiophene-2-carbonyl azide수율 59.5%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

oxalyl chloride (460 mg, 3.62 mmol) followed by N,N-dimethylformide (0.05 mL) was added to a solution of 5-chloro-4-nitrothiophene-2-carboxylic acid (1.0 g, 14.0 mmol) in dichloromethane (20 mL) under nitrogen atmosphere and the resulting mixture was stirred at ambient temperature for 4 hours. TLC analysis showed no acid remaining so the mixture was allowed to be concentrated in vacuo. The resulting acid chloride was dissolved in dry tetrahydrofuran (10 mL). Sodium azide (190 mg, 2.89 mmol) was added to the above solution. The resulting mixture was stirred at ambient temperature for 10 hours. After this time, TLC analysis showed no acid chloride remaining so the mixture was diluted with ethyl acetate and washed with water and brine. The organic layer was separated, dried (Na2SO4), filtered and the solvent was removed to afford the title product as a brown solid (400 mg, 59% yield). 1H NMR (400 MHz, d6-DMSO) δ: 8.23 (2H, s).

후처리

  1. concentrationto be concentrated in vacuo
  2. dissolutionThe resulting acid chloride was dissolved in dry tetrahydrofuran (10 mL)
  3. stirringThe resulting mixture was stirred at ambient temperature for 10 hours
  4. washwashed with water and brine
  5. customThe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent was removed

출처 및 근거

ORD 기록
ord-b67d085af0f1418fab4a0c32fc30241f
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680139B2

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