Hydrochloric Acid → 1-(Phenyl(tetrahydrofuran-2-yl)methyl)urea

HRID 590785ノート

反応式

HRID 590785 の反応式
Cl.[C:2]1([CH:8]([CH:10]2[CH2:14][CH2:13][CH2:12][O:11]2)[NH2:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-:15][C:16]#[N:17].[K+].Cl.C([O-])(O)=O.[Na+]>O.CCOC(C)=O>[C:2]1([CH:8]([CH:10]2[CH2:14][CH2:13][CH2:12][O:11]2)[NH:9][C:16]([NH2:17])=[O:15])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 11378442Potassium cyanateHCID 45791440Oxolan-2-yl(phenyl)methanamine hydrochloride

生成物 1

HCID 1182717571-(Phenyl(tetrahydrofuran-2-yl)methyl)urea

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

Phenyl(tetrahydrofuran-2-yl)methanamine HCl (640 mg, 2.99 mmol) was taken up in water (3 ml). Potassium cyanate (1215 mg, 14.97 mmol) and HCl (3 ml, 36.5 mmol) were then added. The reaction mixture was allowed to stir under microwave irradition at 80° C. for 1 hr. Saturated NaHCO3 and EtOAc were added. The products were extracted into EtOAc (3×). The combined organic layers were washed with brine, dried over MgSO4, and concentrated in vacuo to give 1-(phenyl(tetrahydrofuran-2-yl)methyl)urea. 1H NMR (ppm, 500 MHz, DMSO-d6) δ 7.23 (m, 4H), 7.18 (m, 1H), 6.43 (d, J=9.5, 1H), 5.57 (br s, 2H), 4.68-4.47 (dd, J=3.5, J=5.5, 1H), 3.97 (m, 1H), 3.76 (q, J=8.0 1H), 3.56 (q, J=7.0, 1H), 1.79-1.75 (m, 3H), 1.73 (m, 1H).

後処理

  1. extractionThe products were extracted into EtOAc (3×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-4b6d42c2c4434203a208462c36ff9777
出典データセット
uspto-grants-2016_01
特許番号
US09233979B2

反応ノート

読み込み中…