Potassium Iodide → (Z)-N-[(2-amino-1,3-thiazol-4-yl)methoxy]benzenecarboximidoyl cyanide

HRID 1528341ノート

反応式

HRID 1528341 の反応式
[OH:1]/[N:2]=[C:3](/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)\[C:4]#[N:5].Cl.Cl[CH2:14][C:15]1[N:16]=[C:17]([NH2:20])[S:18][CH:19]=1.[I-].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.CN(C=O)C>[NH2:20][C:17]1[S:18][CH:19]=[C:15]([CH2:14][O:1]/[N:2]=[C:3](/[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)\[C:4]#[N:5])[N:16]=1

参加物

7

反応物 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 732282-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)HCID 5464219N-Hydroxybenzimidoyl cyanide

生成物 1

HCID 89443882(Z)-N-[(2-amino-1,3-thiazol-4-yl)methoxy]benzenecarboximidoyl cyanide収率 90%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6342Acetonitrile溶媒

実験手順

To a solution of (2Z)-(hydroxyimino)(phenyl)acetonitrile (2.5 g, 17.10 mmol, 1 eq.) in 100 ml of acetonitrile and 10 ml DMF was added 4-(chloromethyl)-1,3-thiazol-2-amine hydrochloride (3.79 g, 20.52 mmol, 1.2 eq.) followed by potassium iodide (283 mg, 1.71 mmol, 0.1 eq.) and caesium carbonate (13.37 g, 41.05 mmol, 2.4 eq.). The reaction was stirred overnight at room temperature. The solvent was then evaporated and the residue dissolved in EtOAc (100 ml). The organic layer was washed with H2O and dried over MgSO4 then concentrated. (2Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(phenyl)acetonitrile (4 g, 90% yield, only 1 oxime isomer) was obtained as a white solid.

後処理

  1. customThe solvent was then evaporated
  2. dissolutionthe residue dissolved in EtOAc (100 ml)
  3. washThe organic layer was washed with H2O
  4. dry with materialdried over MgSO4
  5. concentrationthen concentrated

出典と根拠

ORDレコード
ord-b941f558737340e3a36bf5c68caf4ba2
出典データセット
uspto-grants-2015_07
特許番号
US09090600B2

反応ノート

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