Potassium Iodide → 4-[({[(3,4-Dichloro-1,2-thiazol-5-yl)(3-thienyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-amine

HRID 875197ノート

反応式

HRID 875197 の反応式
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([C:8]([C:11]2[CH:15]=[CH:14][S:13][CH:12]=2)=[N:9][OH:10])[S:4][N:3]=1.Cl.Cl[CH2:18][C:19]1[N:20]=[C:21]([NH2:24])[S:22][CH:23]=1.[I-].[K+].N12CCCC1=NCCC2>C(#N)C>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([C:8](=[N:9][O:10][CH2:18][C:19]2[N:20]=[C:21]([NH2:24])[S:22][CH:23]=2)[C:11]2[CH:15]=[CH:14][S:13][CH:12]=2)[S:4][N:3]=1

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 732282-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)HCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 1363312531-(3,4-dichloro-1,2-thiazol-5-yl)-N-hydroxy-1-(3-thienyl)methanimine

生成物 1

HCID 866507364-[({[(3,4-Dichloro-1,2-thiazol-5-yl)(3-thienyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-amine収率 0.7%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

To a stirred suspension of 1-(3,4-dichloro-1,2-thiazol-5-yl)-N-hydroxy-1-(3-thienyl)methanimine (1.60 g, 5.73 mmol), 4-(chloromethyl)-1,3-thiazol-2-amine hydrochloride (937 mg, 6.30 mmol) and potassium iodide (951 mg, 5.73 mmol) in acetonitrile (15 mL) at 0° C. was added 1,5-diazabicyclo(4.3.0)non-5-ene (1.44 mL, 12.0 mmol). The mixture was stirred 10 min at 0° C., then overnight at room temperature. After dilution of the reaction mixture with water and extraction with ethyl acetate, the combined organic layers were dried over MgSO4, concentrated in vacuo, and the residue purified by reverse phase HPLC to afford 4-[({[(3,4-dichloro-1,2-thiazol-5-yl)(3-thienyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-amine [16 mg, yield 0.7%].

後処理

  1. customovernight
  2. customat room temperature
  3. extractionAfter dilution of the reaction mixture with water and extraction with ethyl acetate
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customthe residue purified by reverse phase HPLC

出典と根拠

ORDレコード
ord-00aa644909214e9a9a19f99d45f50abb
出典データセット
uspto-grants-2015_03
特許番号
US08981111B2

反応ノート

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