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

HRID 725904Notes

Reaction equation

HRID 725904 reaction equation
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

Participants

7

Reactant 4

HCID 887MethanolHCID 160352-Chloroethyl isocyanate2×HCID 166715-TetralinylamineHCID 240817N-(2-Chloroethyl)urea

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-25442d1c88dd4d3388148f73c5947710
Source dataset
uspto-grants-1998_01
Patent number
US05708015

Reaction notes

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