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

HRID 590785노트

반응식

HRID 590785 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4b6d42c2c4434203a208462c36ff9777
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233979B2

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