Sulfuric Acid → (5,6-Diethyl-3-oxo-2-benzofuran-1(3H)-ylidene)acetonitrile

HRID 437845노트

반응식

HRID 437845 반응식
[N:1]([C:4]1[C:5](=[O:19])[C:6]2[C:11]([C:12](=[O:14])[CH:13]=1)=[CH:10][C:9]([CH2:15][CH3:16])=[C:8]([CH2:17][CH3:18])[CH:7]=2)=[N+]=[N-].S(=O)(=O)(O)O>>[C:4]([CH:13]=[C:12]1[C:11]2[C:6](=[CH:7][C:8]([CH2:17][CH3:18])=[C:9]([CH2:15][CH3:16])[CH:10]=2)[C:5](=[O:19])[O:14]1)#[N:1]

참가 물질

3

반응물 2

HCID 1118Sulfuric AcidHCID 123664032-Azido-6,7-diethylnaphthalene-1,4-dione

생성물 1

HCID 54399111(5,6-Diethyl-3-oxo-2-benzofuran-1(3H)-ylidene)acetonitrile수율 91.7%

실험 절차

2-Azido-6,7-diethyl-1,4-naphthoquinone (6.0 g; 0.024 mole) was added portionwise to cold (0°-5° C.), stirred concentrated sulphuric acid (100 ml) over 2 hours and the red solution stirred at this temperature till no further nitrogen evolution was noticed (ca. 15 mins.). The products from two such reactions carried out simultaneously were poured into 1200 ml of ice-water and the lilac solid filtered off and washed well with water. Recrystallisation from ethanol in the presence of charcoal give the title compound 5.00 g (47%) as an off-white solid of m.p. 147°-158° C. Further recrystallisation gave a white sample of m.p. 159°-168° C. shown by nmr to be a mixture of E and Z isomers. (Found; C, 73.70; H, 5.95; N, 5.94; C14H13NO2 requires; C, 73.99; H, 5.77; N, 6.16%).

후처리

  1. custom(ca. 15 mins.)
  2. filtrationthe lilac solid filtered off
  3. washwashed well with water
  4. customRecrystallisation from ethanol in the presence of charcoal

출처 및 근거

ORD 기록
ord-99321115a94f453082e2760ef43499fa
출처 데이터셋
uspto-grants-1977_06
특허 번호
US04032544

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