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

HRID 520250

반응식

HRID 520250 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-73f9cf3e77cd426a99ba1934ab3f33f5
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09326515B2

연결된 노트

불러오는 중…