Hydrochloric Acid → Methyl (7-iodo-5-nitro-2-oxo-1,3-benzoxazol-3(2H)-yl)acetate

HRID 542029Notes

Reaction equation

[I:1][C:2]1[C:10]2[O:9][C:8](=[O:11])[NH:7][C:6]=2[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][C:23]([O:25][CH3:26])=[O:24].Cl>CN(C)C=O>[I:1][C:2]1[C:10]2[O:9][C:8](=[O:11])[N:7]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:6]=2[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 7-iodo-5-nitro-1,3-benzoxazol-2(3H)-one (1.6 g, 5.3 mmol) in N,N-dimethylformamide (11 mL) at 0° C. was treated with potassium carbonate (1.2 g, 8.4 mmol) followed by methyl bromoacetate (0.75 mL, 7.9 mmol) and stirred at 20° C. for 2 h. The reaction mixture was added dropwise to a solution of 1M HCl (100 mL) at 0° C. and extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to give a crude solid. This material was washed with cold methanol to give the desired product (1.6 g, 79%) as a solid. LCMS for C10H81N2O6 (M+H)+: m/z=378.8.

Workup

extractionextracted with ethyl acetate (2×100 mL)
washThe combined organic extracts were washed with brine (50 mL)
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated
customto give a crude solid
washThis material was washed with cold methanol

Sources & evidence

ORD record: ord-44687b17fa4e407da82b5979b1ca66da
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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