Hydrochloric Acid → HCID 70100788, 화합물

HRID 1278676노트

반응식

HRID 1278676 반응식
[I-].[Na+].C(C1C=C([C:11]2[CH:23]=[CH:22][C:14]3[NH:15][C:16](=[O:21])[O:17][C:18]([CH3:20])([CH3:19])[C:13]=3[CH:12]=2)C=CC=1)#C.Cl[Si](C)(C)C.Cl.[C:30](#[N:32])[CH3:31]>O.CS(C)=O>[CH3:20][C:18]1([CH3:19])[O:17][C:16](=[O:21])[N:15]([C:11]2[CH:12]=[C:13]([C:18]#[C:31][C:30]#[N:32])[CH:14]=[CH:22][CH:23]=2)[C:14]2[CH:22]=[CH:23][CH:11]=[CH:12][C:13]1=2

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 6342AcetonitrileHCID 6397ChlorotrimethylsilaneHCID 98141916-(3-Ethynyl-phenyl)-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

생성물 1

HCID 70100788HCID 70100788, 화합물수율 4.6%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

To a stirred mixture of DMSO, acetonitrile and water (9 mL/3 mL/0.5 mL) was added at rt under nitrogen cuprous cyanide (0.193 g, 2.2 mmol), sodium iodide (11 mg, 0.072 mmol), and 6-(3-ethynyl-phenyl)-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one (0.2 g, 0.72 mmol). Chlorotrimethylsilane was then added to the above mixture in a dropwise manner. After addition, the mixture was heated at 50° C. for 72 hours. The reaction mixture was then cooled to rt and treated with 0.5 N aqueous HCl cold solution (50 mL). The precipitate obtained was collected on a filter and washed with water. The solid was purified on a silica gel column (hexane:ethyl acetate/2:1) to give the title compound as an off-white solid (10 mg, 4.6%): mp 212-213° C.; 1H-NMR (CHCl3-d6) δ7.96 (s, 1H), 7.77 (s, 1H), 7.65 (d, 1H, J=7.8 Hz), 7.60 (d, 1H, J=7.69 Hz), 7.51 (d, 1H, J=7.77 Hz), 7.45 (dd, 1H, J=8.67, 2.21 Hz), 7.31 (d, 1H, J=1.55 Hz), 6.91 (d, 1H, J=8.19 Hz), 1.8 (s, 6H); MS (EI) m/z 302 ([M+], 30%).

후처리

  1. additionwas added at rt under nitrogen cuprous cyanide (0.193 g, 2.2 mmol)
  2. additionAfter addition
  3. temperatureThe reaction mixture was then cooled to rt
  4. customThe precipitate obtained
  5. customwas collected on
  6. filtrationa filter
  7. washwashed with water
  8. customThe solid was purified on a silica gel column (hexane:ethyl acetate/2:1)

출처 및 근거

ORD 기록
ord-cd69af7ffcc04cffafafc260e2fc8eb0
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06444668B1

반응 노트

불러오는 중…