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

HRID 590785Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-4b6d42c2c4434203a208462c36ff9777
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233979B2

Reaction notes

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