Methanol → N-(2,3-Dimethylphenyl)-4,5-dihydro-1,3-oxazol-2-amine

HRID 1079443

반응식

HRID 1079443 반응식
Cl[CH2:2][CH2:3][N:4]=[C:5]=[O:6].[CH3:7][C:8]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10].ClCCNC(N)=O.CO>O1CCCC1.O>[CH3:7][C:8]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:9]=1[NH:10][C:5]1[O:6][CH2:2][CH2:3][N:4]=1

참가 물질

7

반응물 4

HCID 887MethanolHCID 68932,3-DimethylanilineHCID 160352-Chloroethyl isocyanate2회HCID 240817N-(2-Chloroethyl)urea

생성물 1

HCID 211584N-(2,3-Dimethylphenyl)-4,5-dihydro-1,3-oxazol-2-amine수율 84%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Chloroethylisocyanate (Compound 5, Aldrich, 346 mg, 3.3 mmol) was added to a stirred solution of 2,3-dimethylaniline (Aldrich, 400 mg, 3.3 mmol) in tetrahydrofuran (5 ml) at room temperature. After 30 minutes a white precipitate formed. The solid chloroethylurea was collected by vacuum filtration yield: 477 mg (64%): mp 145°-146° C. HNMR (300 MHz, CDCl3) σ 7.00 (m, 3H); 6.72 (br, 1H); 5.19 (br, 1H), 3.59 (m, 2H); 3.49 (m, 2H); 2.30 (s, 3H); 2.18 (s, 3H); Mass spectrum m/e 226.0872 (C1H15C1N2O requires 226.0872). The chlorethylurea (199 mg, 0.88 mmol) was suspended in H2O (4 ml) and CH3OH (4 ml) and heated to reflux for 1 hour. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was dissolved in CH2Cl2 and washed with 1N NaOH (to pH 13). The organic layer was dried over Na2CO3 and concentrated in vacuo to yield 140 mg (84%) of the title compound as a white crystalline solid: mp 112°-113.5° C.; 1H NMR (300 MHz, CDCl3) σ 7.19 (m, 1H); 7.09 (m, 1H), 6.91 (m, 1H); 5.00 (br, s, 1H); 4.40 (t, 2H); 3.70 (t, 2H); 2.30 (s, 3H); 2.15 (s, 3H); Mass spectrum m/e 190.1104 (C11H14N2O requires 190.1106).

후처리

  1. customAfter 30 minutes a white precipitate formed
  2. filtrationThe solid chloroethylurea was collected by vacuum filtration yield: 477 mg (64%)
  3. temperatureto reflux for 1 hour
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in CH2Cl2
  6. washwashed with 1N NaOH (to pH 13)
  7. dry with materialThe organic layer was dried over Na2CO3
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-d786ff694dba45f3abc58cb60a46a1da
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05580892

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