Hydrochloric Acid → HCID 136387778、化合物

HRID 2402909ノート

反応式

HRID 2402909 の反応式
C([S:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[CH:13]=2)=[CH:8][C:7]=1[C:19]([F:22])([F:21])[F:20])(C)(C)C.[ClH:23]>>[ClH:23].[CH3:18][C:14]1[CH:13]=[C:12]([C:9]2[CH:10]=[CH:11][C:6]([SH:5])=[C:7]([C:19]([F:22])([F:20])[F:21])[CH:8]=2)[CH:17]=[CH:16][N:15]=1

参加物

3

反応物 2

HCID 313Hydrochloric AcidHCID 86684913HCID 86684913、化合物

生成物 1

HCID 136387778HCID 136387778、化合物収率 93.9%

反応条件

温度
100 °C

実験手順

4-(4-tert-Butylsulfanyl-3-trifluoromethyl-phenyl)-2-methyl-pyridine (65.1 g, ˜200 mmol) was dissolved in 5 M HCl (800 mL) and the yellowish solution was warmed up and stirred at 100° C. under reflux for 22 h. After cooling (˜1 h) and stirring at room temperature for 0.5 h, the beige suspension was filtered and the filter cake was washed with deionized water (400 mL) and acetone (200 mL) and then dried (50° C./≧10 mbar/24 h) to give 57.4 g (93.9%) of the title compound as an off-white, crystalline powder, mp. >270° C. (dec.). 1H NMR (CDCl3+2 drops TFA, 400 MHz) δ 2.96 (s, 3H), 4.06 (q, J=3.3 Hz, 1H), 7.63 (d, J=8.3 Hz, 1H), 7.74 (dd, J1=8.3 Hz, J2=2.1 Hz, 1H), 7.84 (d, J=1.9 Hz, 1H), 7.93 (dd, J1=6.3 Hz, J2=1.9 Hz, 1H), 7.97 (d, J=1.9, 1H), 8.79 (d, J=6.2 Hz, 1H), 9.96 (s, 14H, TFA), 15.18 (br s, 1H). ESI-MS (m/z) [M−HCl]− 270 (100).

後処理

  1. temperaturethe yellowish solution was warmed up
  2. temperatureunder reflux for 22 h
  3. temperatureAfter cooling (˜1 h)
  4. stirringstirring at room temperature for 0.5 h
  5. filtrationthe beige suspension was filtered
  6. washthe filter cake was washed with deionized water (400 mL) and acetone (200 mL)
  7. customdried (50° C./≧10 mbar/24 h)

出典と根拠

ORDレコード
ord-da49306c2c6e4ce3a10ff6ffc018a6e6
出典データセット
uspto-grants-2014_08
特許番号
US08796471B2

反応ノート

読み込み中…