Cyclohexanol → HCID 21543699, 화합물

HRID 1521579노트

반응식

HRID 1521579 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=S)[CH2:6][CH2:5]2.[CH:13]([NH:15][NH2:16])=O.C1(O)CCCCC1>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH:13]=[N:15][N:16]=[C:7]1[CH2:6][CH2:5]2

참가 물질

5

반응물 3

HCID 7966CyclohexanolHCID 12229HydrazinecarboxaldehydeHCID 573709906-Bromo-3,4-dihydroquinoline-2(1H)-thione

생성물 1

HCID 21543699HCID 21543699, 화합물

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
120 °C

실험 절차

A flask containing the title compound from Example 22, Step A (0.200 g, 0.826 mmol), formic hydrazide (0.099 g, 1.65 mmol) and cyclohexanol (6.00 ml, 0.826 mmol) was heated to 120° C. for 16 hours. The reaction was then cooled to room temperature, poured into water and extracted with ethyl acetate. The organic extracts were combined, washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by flash chromatography on silica gel (0-15% methanol in ethyl acetate) provided the title compound: LCMS m/z 251.90 [M+2+H]+; 1H NMR (500 MHz, CD3OD) δ 9.12 (s, 1H), 7.63-7.54 (m, 3H), 3.19-3.16 (m, 2H), 3.11-3.08 (m, 2H).

후처리

  1. temperatureThe reaction was then cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography on silica gel (0-15% methanol in ethyl acetate)

출처 및 근거

ORD 기록
ord-6be06c346f4441fb80c58f88157a67a7
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073929B2

반응 노트

불러오는 중…