Cyclohexanol → HCID 21543699、化合物

HRID 1521579ノート

反応式

HRID 1521579 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 21543699HCID 21543699、化合物

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-6be06c346f4441fb80c58f88157a67a7
出典データセット
uspto-grants-2015_07
特許番号
US09073929B2

反応ノート

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