Imidazole → HCID 22623067, compound

HRID 840363Notes

Reaction equation

HRID 840363 reaction equation
Cl[C:2]1[C:3]([N+:14]([O-:16])=[O:15])=[CH:4][C:5]2[O:10][CH:9]([CH3:11])[C:8](=[O:12])[NH:7][C:6]=2[CH:13]=1.[NH:17]1[CH:21]=[CH:20][N:19]=[CH:18]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C.[Cu]>[N:17]1([C:2]2[C:3]([N+:14]([O-:16])=[O:15])=[CH:4][C:5]3[O:10][CH:9]([CH3:11])[C:8](=[O:12])[NH:7][C:6]=3[CH:13]=2)[CH:21]=[CH:20][N:19]=[CH:18]1

Participants

7

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 12192069HCID 12192069, compound

Product 1

HCID 22623067HCID 22623067, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

485 mg of 6-chloro-7-nitro-2-methyl-1,4-benzoxazin-3-one is stirred with 136 mg of imidazole and 332 mg of potassium carbonate in 15 ml of DMF with the addition of copper powder for 6 hours at 180° C. It is diluted with ethyl acetate, extracted with brine, and the organic phase is dried. The crude product is purified by column chromatography with ethyl acetate with the addition of ethanol. 88 mg results.

Workup

  1. extractionextracted with brine
  2. customthe organic phase is dried
  3. customThe crude product is purified by column chromatography with ethyl acetate with the addition of ethanol
  4. custom88 mg results

Sources & evidence

ORD record
ord-aa44a61a87094b09ba485fdd6b773c51
Source dataset
uspto-grants-2002_04
Patent number
US06365736B1

Reaction notes

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