1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-(2-chloro-4-nitrophenyl)tetrahydro-1H-imidazo[5,1-c][1,4]oxazine-1,3(2H)-dione

HRID 1625111Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH:2]1[C:7]([OH:9])=O.C1CCN2C(=NCCC2)CC1.[Cl:21][C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:23]=1[N:31]=[C:32]=[O:33]>ClCCCl.C(Cl)Cl>[Cl:21][C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:23]=1[N:31]1[C:7](=[O:9])[CH:2]2[CH2:3][O:4][CH2:5][CH2:6][N:1]2[C:32]1=[O:33]

Participants

Conditions

Temperature: 160 °C

Procedure

To a stirred solution of 3-morphline carboxylic acid (0.100 g; 0.627 mmol), DBU (187 μL; 1.25 mmol) in 1,2-dichloroethane (2.8 mL) was added 2-chloro-4-nitrophenylisocyanate (0.149 g; 0.752 mmol) and the resulting mixture was heated at 160° C. in the microwave for 10 min. The reaction was diluted with methylene chloride (15 mL), washed with 1N HCl (10 mL), sat. NaHCO3 (10 mL) and concentrated under vacuum to give the crude product. The residue was purified by column chromatography eluting with ethyl acetate/hexanes 0 to 40% to give 106 mg of 2-(2-chloro-4-nitrophenyl)tetrahydro-1H-imidazo[5,1-c][1,4]oxazine-1,3(2H)-dione, 1.1.21, (54%).

Workup

washwashed with 1N HCl (10 mL), sat. NaHCO3 (10 mL)
concentrationconcentrated under vacuum
customto give the crude product
customThe residue was purified by column chromatography
washeluting with ethyl acetate/hexanes 0 to 40%

Sources & evidence

ORD record: ord-ca08964299a3430db4e3d459535d80cb
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08779157B2

Reaction notes

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