Thionyl Chloride → 5-(4,5-Dihydrooxazol-2-yl)-2-isopropoxybenzonitrile

HRID 1053752노트

반응식

HRID 1053752 반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH:12]=[CH:13][C:14]=1[O:15][CH:16]([CH3:18])[CH3:17])[C:6]([NH:8][CH2:9][CH2:10][OH:11])=O)#[N:2].S(Cl)(Cl)=O>C(Cl)Cl>[O:11]1[CH2:10][CH2:9][N:8]=[C:6]1[C:5]1[CH:12]=[CH:13][C:14]([O:15][CH:16]([CH3:18])[CH3:17])=[C:3]([CH:4]=1)[C:1]#[N:2]

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 583550313-cyano-N-(2-hydroxyethyl)-4-isopropoxybenzamide

생성물 1

HCID 583549695-(4,5-Dihydrooxazol-2-yl)-2-isopropoxybenzonitrile수율 61%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

3-cyano-N-(2-hydroxyethyl)-4-isopropoxybenzamide was dissolved in DCM (30 mL) and thionyl chloride (1.43 g, 12 mmol) was added at 0° C. The reaction mixture was stirred at room temperature for 1 h and then quenched at 0° C. with water (200 μL) and 6N NaOH solution (1 mL). The mixture was stirred for 30 min. The aqueous layers were extracted with DCM and the combined organic extracts were washed with brine and dried over MgSO4 to afford 570 mg (61% for two steps) of 5-(4,5-dihydrooxazol-2-yl)-2-isopropoxybenzonitrile INT-31. LCMS-ESI (m/z) calculated for C13H14N2O2: 230.3; found 231.0 [M+H]+, tR=2.50 min. 1H NMR (400 MHz, CDCl3) δ 8.17-7.86 (m, 2H), 6.91 (d, J=8.9 Hz, 1H), 4.65 (dt, J=12.2, 6.1 Hz, 1H), 4.37 (dd, J=14.3, 4.9 Hz, 2H), 3.98 (t, J=9.5 Hz, 2H), 1.36 (t, J=5.5 Hz, 6H).

후처리

  1. customquenched at 0° C. with water (200 μL) and 6N NaOH solution (1 mL)
  2. stirringThe mixture was stirred for 30 min
  3. extractionThe aqueous layers were extracted with DCM
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4

출처 및 근거

ORD 기록
ord-a389be423db448ed976d1189315ee196
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394264B2

반응 노트

불러오는 중…