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

HRID 520250

反応式

HRID 520250 の反応式
[OH:1]/[N:2]=[C:3](/[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=1)\[C:4]#[N:5].Cl.Cl[CH2:16][C:17]1[N:18]=[C:19]([NH2:22])[S:20][CH:21]=1.[I-].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.CN(C=O)C>[NH2:22][C:19]1[S:20][CH:21]=[C:17]([CH2:16][O:1]/[N:2]=[C:3](/[C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=2)\[C:4]#[N:5])[N:18]=1

参加物

7

反応物 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 732282-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)HCID 23502058(2Z)-2-hydroxyimino-2-(3-methoxyphenyl)acetonitrile

生成物 1

HCID 89655523(1Z)-N-[(2-amino-1,3-thiazol-4-yl)methoxy]-3-methoxybenzenecarboximidoyl cyanide収率 91%

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)(3-methoxyphenyl)acetonitrile (2.57 g, 14.59 mmol, 1 eq.) in 70 ml of acetonitrile and 7 ml of DMF, was added 4-(chloromethyl)-1,3-thiazol-2-amine hydrochloride (2.87 g, 16.05 mmol, 1.1 eq.) followed by potassium iodide (242 mg, 1.46 mmol, 0.1 eq.) and caesium carbonate (10.45 g, 32.09 mmol, 2.2 eq.). The reaction was stirred 8 h at room temperature. The solvent was then evaporated and the residue dissolved in EtOAc, subsequently washed with H2O and brine. Ater separation, the organic phase was dried over MgSO4 then concentrated to afford (2Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(3-methoxyphenyl)acetonitrile (4.03 g, 91% yield, only 1 oxime isomer) which was used in the next step without further purification.

後処理

  1. customThe solvent was then evaporated
  2. dissolutionthe residue dissolved in EtOAc
  3. washsubsequently washed with H2O and brine
  4. customAter separation
  5. dry with materialthe organic phase was dried over MgSO4
  6. concentrationthen concentrated

出典と根拠

ORDレコード
ord-73f9cf3e77cd426a99ba1934ab3f33f5
出典データセット
uspto-grants-2016_05
特許番号
US09326515B2

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