Isopropanol → 4-(3-Bromophenyl)oxane-4-carboxamide

HRID 1699112Notes

Reaction equation

CC([OH:4])C.[Br:5][C:6]1[CH:7]=[C:8]([C:12]2([C:18]#[N:19])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:9]=[CH:10][CH:11]=1.[OH-].[K+]>CS(C)=O>[Br:5][C:6]1[CH:7]=[C:8]([C:12]2([C:18]([NH2:19])=[O:4])[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[CH:9]=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 82 °C

Procedure

Propan-2-ol (100 ml), tetrahydro-4-(3-bromophenyl)-2H-pyran-4-nitrile (20.0 g, 0.075 mole, 1 eq.), potassium hydroxide (13.74 g, 0.245 mole, 3.26 eq.) were added to a reaction flask set for boiling at reflux under a nitrogen atmosphere, and the reaction mixture was heated with stirring at reflux, about 82° C. for 5-6 hours under nitrogen. After reaction completion, the mixture was cooled (<30° C.) and quenched with water (100 ml). The resultant slurry was filtered and the product residue, washed with water (30 ml), and dried under vacuum at 45-50° C. to yield a white solid. Yield 19.05 g, 89.2% mp 245-247° C.; m/z 285 (m+1); 1H NMR (300 MHz, DMSO) § 7.43 (m, 5H), 7.14 (s, 1H), 3.76 (d, 2H), 3.47 (t, 2H), 2.44 (d, 2H), 1.79 (m, 2H).; IR (drifts) vmax 3363, 3174, 3062, 2973, 2935, 2879, 2828, 1685, 1631, 1588.

Workup

temperatureat reflux under a nitrogen atmosphere
temperaturethe reaction mixture was heated
customAfter reaction completion
temperaturethe mixture was cooled (<30° C.)
customquenched with water (100 ml)
filtrationThe resultant slurry was filtered
washthe product residue, washed with water (30 ml)
customdried under vacuum at 45-50° C.
customto yield a white solid

Sources & evidence

ORD record: ord-05fd3f9c3e044429a2a91eaf1fec238c
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06344563B1

Reaction notes

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