Water → 2-chloro-6H-benzo[e]benzo[4,5]imidazo[1,2-c][1,3]oxazine

HRID 1776877Notes

Reaction equation

[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[OH:17].Br[CH2:19]Br.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Cl:16][C:14]1[CH:13]=[CH:12][C:11]2[O:17][CH2:19][N:1]3[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=[C:2]3[C:10]=2[CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-(1H-benzo[d]imidazol-2-yl)-4-chlorophenol (80 mg, 0.33 mmol), dibromo-methane (341 mg, 1.96 mmol), K2CO3 (137 mg, 0.99 mmol) in DMF (6 mL) was allowed to stir at 80° C. for 12 hours. Water (20 mL) was added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over Na2SO4. After being concentrated in vacuo, the resulting resulting residue was purified using prep-HPLC to provide 2-chloro-6H-benzo[e]benzo[4,5]imidazo[1,2-c][1,3]oxazine (30 mg, yield: 36%). 1H-NMR (Methanol-d4, 400 MHz) δ 8.07 (d, J=2.1 Hz, 1H), 7.83˜7.81 (m, 1H), 7.78˜7.75 (m, 1H), 7.63 (dd, J=8.8, 2.2 Hz, 1H), 7.54˜7.52 (m, 2H), 7.30 (d, J=8.8 Hz, 1H), 6.33 (s, 2H). MS (M+H)+: 257.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
concentrationAfter being concentrated in vacuo
customthe resulting resulting residue
customwas purified

Sources & evidence

ORD record: ord-8ac901c9555347bba995d32c66a993b0
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09265773B2

Reaction notes

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