Methanol → 2-(5,6,7,8-Tetrahydro-1-naphthylamino)-2-oxazoline

HRID 725904

반응식

HRID 725904 반응식
Cl[CH2:2][CH2:3][N:4]=[C:5]=[O:6].[C:7]1([NH2:17])[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[CH:10]=[CH:9][CH:8]=1.ClCCNC(N)=O.CO>O1CCCC1.O>[C:7]1([NH:17][C:5]2[O:6][CH2:2][CH2:3][N:4]=2)[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[CH:10]=[CH:9][CH:8]=1

참가 물질

7

반응물 4

HCID 887MethanolHCID 160352-Chloroethyl isocyanate2회HCID 166715-TetralinylamineHCID 240817N-(2-Chloroethyl)urea

생성물 1

HCID 988172-(5,6,7,8-Tetrahydro-1-naphthylamino)-2-oxazoline

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Chloroethylisocyanate (Compound 5 210 mg, 2.05 mmol) was added to a stirred solution at 5,6,7,8-tetrahydro-1-naphthylamine (302 mg, 2.05 mmol) in tetrahydrofuran (2 ml). After 30 minutes the resulting chloroethylurea was collected by vacuum filtration. Yield: 302 mg (58%) of fine white crystals: mp 101°-103°; H NMR (300 MHz, CDCl3) σ 6.98-7.30 (m, 3H); 6.08 (brs, 1H); 5.19 (br, s, 1H); 3.68 (m, 2H); 3.55 (m, 2H); 2.79 (m, 2H); 2.61 (m, 2H); 1.80 (m, 4H); Mass spectrum m/e 252.1034 (C13H17ClN2O requires 252.1029). The chloroethyl urea (237 mg, 0.94 mmol) was suspended in H2O (3 ml) and CH3OH (3 ml) and heated to reflux for 18 hours. The reaction mixture was cooled to room temperature and worked up as above to yield after recrystallization (hexane/CHCl3) 187.6 mg (87%) of the title compound: mp 160°-162° C.; 1H NMR (300 MHz, CDCl3) σ 7.23 (m, 1H); 7.08 (m, 1H; 6.75 (m, 1H); 5.55 (br, 1H); 4.35 (t, 2H); 3.70 (t, 2H); 2.70 (m, 2H); 2.58 (m, 2H); 1.80 (m, 4H); Mass spectrum m/e 216.1257 (C13H16N2O requires 216.1262).

후처리

  1. filtrationAfter 30 minutes the resulting chloroethylurea was collected by vacuum filtration
  2. temperatureto reflux for 18 hours
  3. customto yield
  4. customafter recrystallization (hexane/CHCl3) 187.6 mg (87%) of the title compound

출처 및 근거

ORD 기록
ord-25442d1c88dd4d3388148f73c5947710
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05708015

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