Hydrochloric Acid → (1-(3-chloro-2-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochloride

HRID 1842892ノート

反応式

HRID 1842892 の反応式
[Cl:1][C:2]1[C:3]([O:19][CH3:20])=[C:4]([N:8]2[C:12]([C:13]#[N:14])=[CH:11][C:10]([C:15]([F:18])([F:17])[F:16])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.CCOCC.Cl.C(Cl)(Cl)Cl.CO>C1COCC1>[ClH:1].[Cl:1][C:2]1[C:3]([O:19][CH3:20])=[C:4]([N:8]2[C:12]([CH2:13][NH2:14])=[CH:11][C:10]([C:15]([F:17])([F:18])[F:16])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 21584188Chloroform methanolHCID 708164511-(3-chloro-2-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonitrile

生成物 1

HCID 70816406(1-(3-chloro-2-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochloride収率 6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 1-(3-chloro-2-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonitrile (2.03 g, 6.74 mmol, 1.0 eq) in THF (20 mL) was added BH3-DMS (0.512 g, 6.74 mmol, 1.0 eq) at 0° C. and heated to reflux for 3 h. The reaction mixture was cooled to 0° C. and quenched with 1N HCl and basified with 1N solution of NaOH to a pH of ˜10 and extracted with ethyl acetate (100 mL×2), dried (Na2SO4), the solvent evaporated to get a pale yellow oil. The oil was treated with ether and HCl to get (1-(3-chloro-2-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochloride (0.20, 6% yield over 3 steps) as an off white solid (TLC system: CHCl3/MeOH (9:1), Rf 0.5).

後処理

  1. temperatureheated
  2. temperatureto reflux for 3 h
  3. customquenched with 1N HCl
  4. extractionextracted with ethyl acetate (100 mL×2)
  5. dry with materialdried (Na2SO4)
  6. customthe solvent evaporated
  7. customto get a pale yellow oil

出典と根拠

ORDレコード
ord-6b57c44b1a00442bab84e5f32e112adc
出典データセット
uspto-grants-2015_02
特許番号
US08946204B2

反応ノート

読み込み中…