Hydrochloric Acid → HCID 14478919, 화합물

HRID 620004노트

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HRID 620004 반응식
[CH3:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[C:6]([NH:11][C:12](=[O:14])[CH3:13])[C:3]=1[C:4]#[N:5].Cl.[Br:16]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>O.C(Cl)(Cl)(Cl)Cl>[CH3:1][C:2]1[C:9]([CH2:10][Br:16])=[CH:8][CH:7]=[C:6]([NH:11][C:12](=[O:14])[CH3:13])[C:3]=1[C:4]#[N:5]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6547Azobisisobutyronitrile2회HCID 67184N-bromobutanimideHCID 144789182,3-Dimethyl-6-acetamidobenzonitrile

생성물 1

HCID 14478919HCID 14478919, 화합물수율 42.3%

시약·촉매·용매 2

HCID 962Water용매HCID 5943Carbon Tetrachloride용매

실험 절차

In a carefully dried Pyrex reaction vessel were combined 10 g of 2,3-dimethyl-6-acetamidobenzonitrile, 300 ml of CCl4, and 200 ml of HCl-free CHCl3 under argon. To this solution was added 10.8 g of N-bromosuccinimide (recrystallized from H2O) and 0.5 g of azo bisisobutyronitrile (AIBN). The reaction was heated to reflux and irradiated with an external General Electric sunlamp. The initially yellow reaction turned red-brown after 1 h when an additional 0.5 g of AIBN was added. After another 2 h, the reaction mixture was poured into H2O, separated, and the aqueous layer reextracted with CHCl3. The combined CHCl3 layers were washed with H2O, saturated NaHCO3 solution, and brine. The dried organic solution was evaporated at reduced pressure and the residue was crystallized from ethyl acetate to yield 6 g (42%) of the title compound, m.p. 152°-153° C. NMR (CDCl3) 2.30 (3H, s, CH3CON), 2.60 (3H, s, CH3), 4.50 (2H, s, --CH2Br), 7.40 (1H, d, ArH), 8.10 (1H, d, ArH), Anal. Calc'd for C11H11BrN2O: C, 49.5; H, 4.15; N, 10.5. Found: C, 50.3, H, 4.31; N, 10.6.

후처리

  1. customIn a carefully dried Pyrex reaction vessel
  2. temperatureThe reaction was heated
  3. temperatureto reflux
  4. customirradiated with an external General Electric sunlamp
  5. customThe initially yellow reaction
  6. waitAfter another 2 h
  7. customseparated
  8. washThe combined CHCl3 layers were washed with H2O, saturated NaHCO3 solution, and brine
  9. customThe dried organic solution was evaporated at reduced pressure
  10. customthe residue was crystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-aa6e0cd6454c4854b73e2b74a6816f25
출처 데이터셋
uspto-grants-1989_04
특허 번호
US04818753

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