Acetic Acid → N-(2-chloroethyl)-N-nitrosocarbamoylazide

HRID 903496

반응식

HRID 903496 반응식
[N+:1]([O-])([N+]([O-])=O)=[O:2].C([O-])(=O)C.[Na+].[Cl:12][CH2:13][CH2:14][NH:15][C:16]([N:18]=[N+:19]=[N-:20])=[O:17].CC(O)=O>C(Cl)(Cl)(Cl)Cl>[Cl:12][CH2:13][CH2:14][N:15]([N:1]=[O:2])[C:16]([N:18]=[N+:19]=[N-:20])=[O:17]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 25352Nitrogen oxide (N2O4)HCID 517045Sodium AcetateHCID 13481262(2-Chloroethyl)carbamyl azide

생성물 1

HCID 10654895N-(2-chloroethyl)-N-nitrosocarbamoylazide

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

반응 조건

온도
0 °C

실험 절차

Nitrogen tetroxide (0,3 mole) was slowly added to a suspension of anhydrous sodium acetate (0.6 mole) in 300 ml of carbon tetrachloride at -10° C. After warming to 0° C., 2-chloroethylcarbamoyl azide (0.2) was slowly added with a spatula to the stirred suspension. A white precipitate was formed (AcOH). After 15 minutes, the reaction mixture was poured into ice water. The separated organic phase was extracted twice with 50 ml of a cold solution of NaHCO3 (1 molar) and was then washed neutral with 2×50 ml of ice cold water saturated with NaCl. It was then dried over anhydrous sodium sulfate. No attempt was made to isolate N-(chloroethyl)-N-nitrosocarbamoyl azide as it is potentially explosive. The NMR spectroscopic examination of the CCl4 solution (internal standard TMS) showed the complete absence of an NH- signal and showed a pattern which is typical for the A2B2 system of the nitrosated 2-chloroethylamino group. δ=3.50 ppm (t, 2H, --CH2 -- N--NO); 4.15 ppm (t, 2H, Cl--CH2 --).

후처리

  1. extractionThe separated organic phase was extracted twice with 50 ml of a cold solution of NaHCO3 (1 molar)
  2. washwas then washed neutral with 2×50 ml of ice cold water saturated with NaCl
  3. dry with materialIt was then dried over anhydrous sodium sulfate

출처 및 근거

ORD 기록
ord-6f1b84a628d045009ade0c25a0bc85f9
출처 데이터셋
uspto-grants-1980_10
특허 번호
US04228086

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