Hydrochloric Acid → [5-(Methanesulfonyl)pyridin-2-yl]methanaminium chloride

HRID 1517474ノート

反応式

HRID 1517474 の反応式
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[N:12])=[N:9][CH:10]=1)(=[O:4])=[O:3].C(O)C.[ClH:16]>[Pd].O>[ClH:16].[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][NH2:12])=[N:9][CH:10]=1)(=[O:4])=[O:3]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 591699295-(Methylsulfonyl)pyridine-2-carbonitrile

生成物 1

HCID 66725223[5-(Methanesulfonyl)pyridin-2-yl]methanaminium chloride収率 84%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 962Water溶媒

反応条件

温度
25 °C

実験手順

To 5-methanesulfonyl-pyridine-2-carbonitrile (3.0 kg, 1 mol eq, limiting reagent) was charged absolute ethanol (30.7 L, 10 rel vol), 32% aqueous 6 M hydrochloride acid (3.9 kg, 2 mol eq) and palladium on carbon (303 g, 1.50 g, 10% w/w). The reaction was stirred under a hydrogen atmosphere (2.5 bar) at 25° C. until the reaction was complete as judged by HPLC analysis. Water (5.4 L, 1.8 rel vol) was charged. The mixture was filtered through Celite and washed with water (1.8 L, 0.6 rel vol). The reaction mixture was concentrated under reduced pressure and ethanol (30.0 L, 10 rel vol) charged. The mixture was cooled, stirred and the product collected by filtration. The solid was washed with ethanol (16.9 L, 5.6 rel vol) and the solid dried to constant weight yielding the title compound (3.1 kg, 13.8 mol, 84%); 1H NMR (d6-DMSO): 9.10 (d, 1H, J=2.4 Hz), 8.73 (br s, 3H), 8.41 (dd, 1H, J 2.4, 8.3 Hz), 7.82 (d, 1H, J=8.2 Hz), 4.30-4.34 (m, 2H), 3.35 (s, 3H) ppm; LCMS: m/z 187.3 (MH+).

後処理

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with water (1.8 L, 0.6 rel vol)
  3. concentrationThe reaction mixture was concentrated under reduced pressure and ethanol (30.0 L, 10 rel vol)
  4. additioncharged
  5. temperatureThe mixture was cooled
  6. stirringstirred
  7. filtrationthe product collected by filtration
  8. washThe solid was washed with ethanol (16.9 L, 5.6 rel vol)
  9. customthe solid dried to constant weight

出典と根拠

ORDレコード
ord-bf6e4b4d17d44bbcae94027d50081885
出典データセット
uspto-grants-2012_07
特許番号
US08232296B2

反応ノート

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