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

HRID 875223ノート

反応式

HRID 875223 の反応式
[OH:1][N:2]=[C:3]([C:9]1[N:13]([CH3:14])[CH:12]=[N:11][CH:10]=1)[C:4]1[S:5][CH:6]=[CH:7][CH:8]=1.Cl.Cl[CH2:17][C:18]1[N:19]=[C:20]([NH2:23])[S:21][CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(#N)C>[CH3:14][N:13]1[C:9]([C:3](=[N:2][O:1][CH2:17][C:18]2[N:19]=[C:20]([NH2:23])[S:21][CH:22]=2)[C:4]2[S:5][CH:6]=[CH:7][CH:8]=2)=[CH:10][N:11]=[CH:12]1

参加物

6

反応物 4

HCID 4875Potassium Iodide2 回HCID 10796Cesium carbonateHCID 732282-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)HCID 86650754N-hydroxy-1-(1-methyl-1H-imidazol-5-yl)-1-(2-thienyl)methanimine

生成物 1

HCID 866507564-[({[(1-methyl-1H-imidazol-5-yl)(2-thienyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-amine収率 24.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of N-hydroxy-1-(1-methyl-1H-imidazol-5-yl)-1-(2-thienyl)methanimine (4.08 g, 19.7 mmol) and 4-(chloromethyl)-1,3-thiazol-2-amine hydrochloride (4.01 g, 21.7 mmol) in acetonitrile (50 mL) were added cesium carbonate (13.5 g, 41.4 mmol) and potassium iodide (327 mg, 1.97 mmol). After stirring at room temperature for 51 h, potassium iodide (5.90 g, 35.5 mmol) was added and the mixture was stirred for 72 h at room temperature then at 70° C. for 3.5 h. The reaction mixture was filtered, the insolubles washed with acetone and methanol, and the filtrate concentrated in vacuo, diluted in ethyl acetate (50 mL), washed with water (2×30 mL), dried over MgSO4 and concentrated to dryness in vacuo. Purification of the residue on silica gel afforded 4-[({[(1-methyl-1H-imidazol-5-yl)(2-thienyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-amine [1.54 g, yield 23%; HPLC/MS: m/z=320 (M+H); log P(HCOOH)=0.22].

後処理

  1. stirringthe mixture was stirred for 72 h at room temperature
  2. waitat 70° C. for 3.5 h
  3. filtrationThe reaction mixture was filtered
  4. washthe insolubles washed with acetone and methanol
  5. concentrationthe filtrate concentrated in vacuo
  6. additiondiluted in ethyl acetate (50 mL)
  7. washwashed with water (2×30 mL)
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated to dryness in vacuo
  10. customPurification of the residue on silica gel

出典と根拠

ORDレコード
ord-47585d06c39b4e3480179390214b866f
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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