Stannous Chloride → 2-(4-amino-2-chlorophenyl)tetrahydro-1H-imidazo[5,1-c][1,4]oxazine-1,3(2H)-dione

HRID 1625112Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[C:19](=[O:20])[CH:14]2[CH2:15][O:16][CH2:17][CH2:18][N:13]2[C:12]1=[O:21].[Sn](Cl)Cl>C(O)C>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([N:11]2[C:19](=[O:20])[CH:14]3[CH2:15][O:16][CH2:17][CH2:18][N:13]3[C:12]2=[O:21])=[C:2]([Cl:1])[CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 2-(2-chloro-4-nitrophenyl)tetrahydro-1H-imidazo[5,1-c][1,4]oxazine-1,3(2H)-dione (0.106 g, 0.341 mmol) in ethanol (5 mL) was added tin (II) chloride (0.323 g, 1.70 mmol) and the reaction mixture was heated at 80° C. for 15 h. The reaction was cooled to room temperature, quenched with sat. NaHCO3, and the white precipitate was filtered. The filtrate was partitioned between ethyl acetate (20 mL) and brine (15 mL). The organic phase was separated, dried (MgSO4), filtered and concentrated to give the crude product. The residue was purified by column chromatography eluting with ethyl acetate/hexanes 0 to 70% to give 84 mg of 2-(4-amino-2-chlorophenyl)tetrahydro-1H-imidazo[5,1-c][1,4]oxazine-1,3(2H)-dione, 1.2.21, (88%).

Workup

temperatureThe reaction was cooled to room temperature
customquenched with sat. NaHCO3
filtrationthe white precipitate was filtered
customThe filtrate was partitioned between ethyl acetate (20 mL) and brine (15 mL)
customThe organic phase was separated
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
customto give the crude product
customThe residue was purified by column chromatography
washeluting with ethyl acetate/hexanes 0 to 70%

Sources & evidence

ORD record: ord-ab1acd887dbc4312a9f8ed6f3338694b
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08779157B2

Reaction notes

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