Sulfuric Acid → 7-Nitro-2,3-dihydro-1,5-benzoxazepin-4(5H)-one

HRID 1687562

반응식

HRID 1687562 반응식
ClC(Cl)(Cl)C(O)=O.S(=O)(=O)(O)O.[N+:13]([C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[O:22][CH2:21][CH2:20][C:19]2=[O:26])([O-:15])=[O:14].[N-:27]=[N+]=[N-].[Na+]>>[N+:13]([C:16]1[CH:25]=[CH:24][C:23]2[O:22][CH2:21][CH2:20][C:19](=[O:26])[NH:27][C:18]=2[CH:17]=1)([O-:15])=[O:14]

참가 물질

5

반응물 4

HCID 1118Sulfuric AcidHCID 6421Trichloroacetic AcidHCID 33557Sodium AzideHCID 52288316-nitro-3,4-dihydro-2H-1-benzopyran-4-one

생성물 1

HCID 574159447-Nitro-2,3-dihydro-1,5-benzoxazepin-4(5H)-one수율 22%

반응 조건

온도
70 °C

실험 절차

Trichloroacetic Acid (39 g, 0.24 mol), Sulfuric acid (3 mL, 0.05 mol), and 6-Nitro-chroman-4-one (5.000 g, 0.026 mol) were combined and heated to 70° C. Sodium azide (3.36 g, 0.052 mol) was added slowly. The resulting solution was heated for 2 h, poured onto ice. Title compound isolated as a beige solid in 22% yield. 95% purity, LCMS: 209.15 (M+1) 1H NMR (400 MHz, DMSO, d6) δ 10.13, (s, 1H), 8.06 (dd, J=1.5 Hz, 1H), 7.85-7.82 (m, 1H), 7.15 (d, J=8.8 Hz, 1H), 4.47-4.44 m, 2H), 2.88-2.85 (m, 2H).

후처리

  1. temperatureThe resulting solution was heated for 2 h
  2. additionpoured onto ice

출처 및 근거

ORD 기록
ord-f8a03911af4b4f24b0cba09c60da11e7
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148391B2

연결된 노트

불러오는 중…