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

HRID 1053752ノート

反応式

HRID 1053752 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a389be423db448ed976d1189315ee196
出典データセット
uspto-grants-2016_07
特許番号
US09394264B2

反応ノート

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